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Chicago captivates visitors year-round with its striking skyline, bustling neighborhoods, and scenic lakefront. From the iconic Cloud Gate sculpture (affectionately known as "The Bean") to historic Wrigley Field, this guide highlights the must-see Chicago experiences that draw millions of tourists annually.

Tourists interested in art, architecture, food, sports, and family fun will find memorable experiences in every corner of the Windy City. Grab your walking shoes and prepare to discover what makes this Midwestern city a favorite destination for travelers worldwide.

Must-Do Chicago Tourist Attractions for First-Time Visitors:

These are just a few of the most iconic Chicago locations and activities that first-time visitors to Chicago won’t want to miss!

Millennium Park

Millennium Park is known as Chicago’s front yard, and is a popular stop for first-time tourists. Stroll the grounds and see the iconic Cloud Gate, affectionately known as "The Bean.” During summer months, you can find free workout classes on the Great Lawn, catch concerts at the Jay Pritzker Pavilion, or let kids splash in Crown Fountain's interactive water displays. In winter, the park becomes a holiday wonderland, with ice skating at McCormick Tribune Ice Rink and special events throughout the season.

Millenium Park

Lincoln Park & Zoo

Lincoln Park is a sprawling, 1,200-acre public space where visitors can find natural beauty and cultural attractions. In the Lincoln Park Conservatory, you can enjoy year-round tropical warmth and stunning flower displays. The Lincoln Park Zoo is one of North America's oldest free zoos and is home to over 200 species of animals. The zoo's free admission policy makes it a popular tourist location.

Tiger at the Lincoln Park Zoo

360 CHICAGO

Get a bird's-eye view of the city on the observation deck 1,000 feet above the Magnificent Mile at 360 CHICAGO. Here, you’ll find unmatched views of the city skyline and Lake Michigan. For an extra thrill, try TILT – an enclosed moving platform that angles you outward for a face-first view of the city below. After your exhilarating ride, stop by CloudBar for craft cocktails while you watch the sunset over the Chicago skyline.

Views at 360 CHICAGO

Try Deep Dish Pizza

Chicago's signature dish deserves dedicated exploration. Each pizzeria offers its own interpretation, and you’ll find lots of strong opinions about which is best. Just remember that traditional deep dish takes up to 45 minutes to prepare, so dedicate some time to the experience if you’re eating in-restaurant. Many locations offer pre-orders for pickup, so be sure to call ahead if you’d rather take your deep dish to go.

Deep Dish Pizza

Special-Interest Locations:

If you have time during your visit to the Windy City, check out one of these special-interest locations.

Wrigley Field

Even those who aren’t baseball fans can appreciate the history and atmosphere of Wrigley Field. The manual scoreboard and ivy-covered walls hint at the history of this iconic field that was built in 1914. The surrounding Wrigleyville neighborhood is full of lively celebrations on game days. On non-game days, baseball fans can book behind-the-scenes tours to see otherwise restricted areas like player facilities and the press box.

Wrigley Field in Chicago

Adler Planetarium

Alder Planetarium was America's first planetarium and combines historic architecture with cutting-edge space science. Domed theaters present immersive sky shows, and interactive exhibits let visitors explore space missions and astronomical phenomena. The Doane Observatory houses the largest public telescope in the Chicago area. The planetarium's location on Northerly Island means you’ll get one of the best skyline views in Chicago, especially at sunset. Visit during one of their special evening events for an extra exciting and educational experience.

Adler Planetarium

Museum of Science and Industry

The massive Museum of Science and Industry, located in Jackson Park, makes science accessible and exciting. The U-505 submarine tour takes visitors inside the only German U-boat captured during World War II. The Giant Dome Theater shows IMAX films, and the Science Storms exhibit explains natural phenomena with interactive displays. The Coal Mine descent has educated visitors about mining since 1933. Plan on spending at least 4 hours at the museum if you plan to explore it thoroughly.

Museum of Science and Industry

Maggie Daley Park

Reimagine what a city park can be when you visit the 20-acre Maggie Daley Park. At the Play Garden, you’ll find custom-designed equipment for different age groups. Depending on the season, you can enjoy ice or roller skating on the quarter-mile Skating Ribbon. Visitors can also take advantage of the climbing walls, mini golf, and tennis courts. Visit early on summer mornings to avoid crowds at the play areas, or come at dusk when the park's lighting creates a magical atmosphere.

Maggie Daley Park

Chicago Children's Museum

Three floors of hands-on exhibits at the Chicago Children’s Museum encourage learning through play. The Tinkering Lab lets kids experiment with real tools and materials. The Dinosaur Expedition recreates a real Chicago fossil dig site. Water City teaches about the Great Lakes ecosystem, and the Treehouse Trails offers safe exploration for toddlers. Morning visits tend to be quieter, especially on weekdays.

Chicago Children's Museum

Top Neighborhoods:

You won’t run out of places to visit or delicious food to try when you spend a day touring any one of these top Chicago neighborhoods.

Logan Square

The historic boulevard district, Logan Square, is one of Chicago's most vibrant neighborhoods. The Logan Theatre, restored to its 1915 glory, shows indie films and hosts special events. The Logan Square Farmers Market operates year-round, moving indoors during winter months. The restored graystones and boulevard system earned Logan Square a spot on the National Register of Historic Places. Visit during the summer to experience the Logan Square Arts Festival.

Logan Square

The Magnificent Mile

While not quite a full neighborhood, the famous stretch of Michigan Avenue known as The Magnificent Mile is home to Chicago's premier shopping and dining district. Along with flagship stores and luxury boutiques, you’ll see architectural landmarks like the Tribune Tower and Wrigley Building. The historic Water Tower, which survived the Great Chicago Fire, can also be seen here. Visit during the holiday season to see spectacular light displays and window decorations.

The Magnificent Mile

Chinatown

In Chicago's Chinatown, you’ll discover authentic Asian culture just minutes from downtown. On Wentworth Avenue, you’ll find dim sum restaurants, bubble tea shops, and specialty stores. Ping Tom Memorial Park is home to peaceful riverside gardens and skyline views, and the Chinese-American Museum explores the community's rich history.

Chinatown in Chicago

Pilsen

Pilsen is a Lower West Side neighborhood that showcases Chicago's Mexican-American heritage with vibrant murals, galleries, and restaurants. Visitors can visit the National Museum of Mexican Art for free to see the rotating exhibits that celebrate Mexican culture. On 18th Street, you’ll find authentic taquerias, vintage shops, and independent art spaces. Visit during the annual Pilsen Food & Wine Festival to sample the area's best cuisine, or join a mural walking tour to learn about the neighborhood's public art.

Pilsen mural

Lakefront Fun:

Lake Michigan is home to all kinds of fun activities and interesting sights for first-time tourists and locals alike.

Navy Pier

Navy Pier extends into Lake Michigan and is home to a mix of family entertainment and lakefront scenery. The Centennial Wheel rises 200 feet above the pier, with stunning views of the Chicago skyline and lake. When it’s time to eat, you can choose anything from casual Chicago-style hot dogs or upscale dining with waterfront views. In the summer, catch spectacular fireworks displays on Wednesday and Saturday nights. The pier is typically less crowded on weekday mornings, and there are plenty of indoor attractions to see on rainy or cold days.

Navy Pier

Chicago Riverwalk

The Chicago Riverwalk is a 1.25-mile pedestrian pathway that turned this former industrial waterfront area into one of Chicago's most popular destinations. Stop at the Vietnam Veterans Memorial Plaza for a moment of reflection, or watch boats navigate the river's locks near Michigan Avenue. The walk is particularly beautiful during the morning and evening golden hours when sunlight plays off the surrounding architecture.

Chicago Riverwalk

Chicago Boat Tours

Boat tours are a unique way to see the city skyline from Lake Michigan and the Chicago River. You’ll find a variety of boat tours and cruises at Navy Pier. Sightseeing cruises glide past iconic buildings. Dining cruises pair stunning views with upscale meals. Thrill-seekers can opt for high-speed rides that zip across Lake Michigan, and families can find more relaxed tours that are fun for everyone. Book a morning cruise for calmer waters and smaller crowds, or choose a sunset cruise to watch the city lights come alive.

Chicago Downtown Boat Tours

Shedd Aquarium

At Shedd Aquarium, you’ll get an immersive look at aquatic life from around the world and have the chance to see over 32,000 animals. The Caribbean Reef exhibit, a 90,000-gallon circular tank in the central rotunda, features regular diver presentations. Visit during feeding times for the most active animal encounters. Early afternoon tends to be the most crowded time to visit, so morning visits can mean shorter lines.

Shedd Aquarium

Cultural Experiences:

Tourists looking for culture in the city won’t be disappointed. Chicago is home to a wide variety of museums and cultural experiences of all kinds.

Art Institute of Chicago

The Art Institute of Chicago on Michigan Avenue is home to one of the world’s finest art collections. The Modern Wing houses an impressive collection of 20th and 21st-century art, and the older galleries contain countless masterpieces, including "American Gothic" and Monet's "Water Lilies." Illinois residents can take advantage of free admission Thursday evenings. The museum's Ryan Learning Center also offers free family programs on weekends.

Art Institute of Chicago

Field Museum

The Field Museum is one of the world's largest natural history museums. SUE, the most complete skeleton of a T-Rex ever found, resides in the main hall. The museum's extensive collection also includes mummies from ancient Egypt, precious gems, and Native American artifacts. Plan at least half a day to explore. The third-floor houses fascinating anthropology collections that are often missed by casual visitors. Visit on the first and second Wednesdays of each month for free admission if you're an Illinois resident.

Field Museum

Chicago Food Tours

Explore the flavor of Chicago's diverse neighborhoods with Chicago Food & City Tours. Tours range from downtown deep-dish adventures to explorations of iconic neighborhoods like Little Italy and Pilsen. Many tours combine food tastings with architectural and historical information. If you’ll be visiting Chicago for an extended period of time, booking a food tour at the beginning of your trip is an excellent way to get recommendations for the rest of your stay.

Chicago Food Tours

Chicago Cultural Center

The Chicago Cultural Center, known as "The People's Palace," occupies an entire city block in the heart of downtown. The building's two stunning stained-glass domes include the world's largest Tiffany glass dome, which spans 38 feet in diameter. Visitors can find daily programs in this historic space, including free music performances, art exhibitions, and cultural celebrations. Take a free building tour to discover hidden architectural details and learn how this structure served as Chicago's first public library.

Chicago Cultural Center

Chicago Shakespeare Theater

Located near Navy Pier, the world-class Chicago Shakespeare Theatre presents quality productions in an intimate setting. The main theater's design means no seat is more than 30 feet from the action. Along with Shakespeare, the theater presents musicals, international productions, and family programming. The TheaterBox space hosts experimental works and visiting companies. Arrive early to explore the lobby exhibits about current productions.

Chicago Shakespeare Theater

Plan Your Tour of Chicago

Chicago holds an impressive mix of architectural marvels, cultural sites, beautiful parks, and unique neighborhoods that appeal to visitors of all ages. Make 360 CHICAGO Observation Deck a priority stop on your tour, and add excitement to your visit with TILT – the attraction that leans you out over Chicago for a one-of-a-kind view from 94 floors up! Book your tickets today and create lasting memories at 360 CHICAGO during your visit to the Windy City!

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There’s always something new to discover around every corner in Chicago. Locals and visitors can fill their days with world-class museums, stunning architecture, peaceful parks, and delicious restaurants. Even if you’ve seen the most popular tourist spots, there’s always more to explore in the Windy City.

We’re sharing some of the best attractions and activities the city has to offer in this ultimate guide!

Millennium Park

Millennium Park is a year-round cultural destination known as Chicago’s front yard. Stroll the grounds and see the iconic Cloud Gate, affectionately known as "The Bean.” During summer months, you can find free workout classes on the Great Lawn, catch concerts at the Jay Pritzker Pavilion, or let kids splash in Crown Fountain's interactive water displays. In winter, the park becomes a holiday wonderland, with ice skating at McCormick Tribune Ice Rink and special events throughout the season.

Millennium Park

Navy Pier

Navy Pier extends into Lake Michigan and is home to a mix of family entertainment and lakefront scenery. The Centennial Wheel rises 200 feet above the pier, with stunning views of the Chicago skyline and lake. When it’s time to eat, you can choose anything from casual Chicago-style hot dogs or upscale dining with waterfront views. In the summer, catch spectacular fireworks displays on Wednesday and Saturday nights. The pier is typically less crowded on weekday mornings, and there are plenty of indoor attractions to see on rainy or cold days.

Navy Pier

Art Institute of Chicago

The Art Institute of Chicago on Michigan Avenue is home to one of the world’s finest art collections. The Modern Wing houses an impressive collection of 20th and 21st-century art, and the older galleries contain countless masterpieces including "American Gothic" and Monet's "Water Lilies." Illinois residents can take advantage of free admission Thursday evenings. The museum's Ryan Learning Center also offers free family programs on weekends.

Art Institute

Chicago Riverwalk

The Chicago Riverwalk is a 1.25-mile pedestrian pathway that turned this former industrial waterfront area into one of Chicago's most popular destinations. Stop at the Vietnam Veterans Memorial Plaza for a moment of reflection, or watch boats navigate the river's locks near Michigan Avenue. The walk is particularly beautiful during morning and evening golden hours when sunlight plays off the surrounding architecture.

Chicago Riverwalk

Field Museum

The Field Museum is one of the world's largest natural history museums. SUE, the most complete skeleton of a T-Rex ever found, resides in the main hall. The museum's extensive collection also includes mummies from ancient Egypt, precious gems, and Native American artifacts. Plan at least half a day to explore. The third-floor houses fascinating anthropology collections that are often missed by casual visitors. Visit on the first and second Wednesdays of each month for free admission if you're an Illinois resident.

Field Museum

Shedd Aquarium

At Shedd Aquarium, you’ll get an immersive look at aquatic life from around the world and have the chance to see over 32,000 animals. The Caribbean Reef exhibit, a 90,000-gallon circular tank in the central rotunda, features regular diver presentations. Visit during feeding times for the most active animal encounters. Early afternoon tends to be the most crowded time to visit, so morning visits can mean shorter lines.

Shedd Aquarium

Adler Planetarium

Alder Planetarium was America's first planetarium and combines historic architecture with cutting-edge space science. Domed theaters present immersive sky shows, and interactive exhibits let visitors explore space missions and astronomical phenomena. The Doane Observatory houses the largest public telescope in the Chicago area. The planetarium's location on Northerly Island means you’ll get one of the best skyline views in Chicago, especially at sunset. Visit during one of their special evening events for an extra exciting and educational experience.

Adler Planetarium

360 CHICAGO

Start your Chicago adventure 1,000 feet above the Magnificent Mile at 360 CHICAGO. Here, you’ll find unmatched views of the city skyline and Lake Michigan from the observation deck. For an extra thrill, try TILT – an enclosed moving platform that angles you outward for a face-first view of the city below. After your exhilarating ride, stop by CloudBar for craft cocktails while you watch the sunset over the Chicago skyline.

360 CHICAGO

The Magnificent Mile

The famous stretch of Michigan Avenue known as The Magnificent Mile is home to Chicago's premier shopping and dining district. Along with flagship stores and luxury boutiques, you’ll see architectural landmarks like the Tribune Tower and Wrigley Building. The historic Water Tower, which survived the Great Chicago Fire, can also be seen here. Visit during the holiday season to see spectacular light displays and window decorations.

The Magnificent Mile

Chinatown

In Chicago's Chinatown, you’ll discover authentic Asian culture just minutes from downtown. On Wentworth Avenue, you’ll find dim sum restaurants, bubble tea shops, and specialty stores. Ping Tom Memorial Park is home to peaceful riverside gardens and skyline views, and the Chinese-American Museum explores the community's rich history.

Chinatown

Lincoln Park

Lincoln Park is a sprawling, 1,200-acre public space where visitors can find natural beauty and cultural attractions. In the Lincoln Park Conservatory, you can enjoy year-round tropical warmth and stunning flower displays. The Nature Boardwalk is a peaceful and beautiful place to walk when you need a break from the city streets.

Lincoln Park

Deep Dish Pizza

Chicago's signature dish deserves dedicated exploration. Each pizzeria offers its own interpretation, and you’ll find lots of strong opinions about which is best. Just remember that traditional deep dish takes up to 45 minutes to prepare, so dedicate some time to the experience if you’re eating in-restaurant. Many locations offer pre-orders for pickup, so be sure to call ahead if you’d rather take your deep dish to go.

Deep Dish Pizza

Chicago Breweries

Chicago's craft beer scene rivals any in the country. Revolution Brewing, the city's largest independent brewery, provides tours of their production facility and has a comfortable taproom where you can enjoy local favorites. Most breweries offer weekend tours that include tastings, but be sure to book tours in advance before they sell out. Visit taprooms during weekday happy hours to avoid crowds and chat with knowledgeable staff about their brewing processes.

Chicago Breweries

Chicago Food Tours

Explore the flavor of Chicago's diverse neighborhoods with Chicago Food & City Tours. Tours range from downtown deep-dish adventures to explorations of iconic neighborhoods like Little Italy and Pilsen. Many tours combine food tastings with architectural and historical information. If you’ll be visiting Chicago for an extended period of time, booking a food tour at the beginning of your trip is an excellent way to get recommendations for the rest of your stay.

Chicago Food Tours

Museum of Science and Industry

The massive Museum of Science and Industry, located in Jackson Park, makes science accessible and exciting. The U-505 submarine tour takes visitors inside the only German U-boat captured during World War II. The Giant Dome Theater shows IMAX films and the Science Storms exhibit explains natural phenomena with interactive displays. The Coal Mine descent has educated visitors about mining since 1933. Plan on spending at least 4 hours at the museum if you plan to explore it thoroughly.

Museum of Science and Industry

Wrigley Field

Even those who aren’t baseball fans can appreciate the history and atmosphere of Wrigley Field. The manual scoreboard and ivy-covered walls hint at the history of this iconic field that was built in 1914. The surrounding Wrigleyville neighborhood is full of lively celebrations on game days. On non-game days, baseball fans can book behind-the-scenes tours to see otherwise restricted areas like player facilities and the press box.

Wrigley Field

Chicago Cultural Center

The Chicago Cultural Center, known as "The People's Palace," occupies an entire city block in the heart of downtown. The building's two stunning stained-glass domes include the world's largest Tiffany glass dome, which spans 38 feet in diameter. Visitors can find daily programs in this historic space, including free music performances, art exhibitions, and cultural celebrations. Take a free building tour to discover hidden architectural details and learn how this structure served as Chicago's first public library.

Chicago Cultural Center

Maggie Daley Park

Reimagine what a city park can be when you visit the 20-acre Maggie Daley Park. At the Play Garden, you’ll find custom-designed equipment for different age groups. Depending on the season, you can enjoy ice or roller skating on the quarter-mile Skating Ribbon. Visitors can also take advantage of the climbing walls, mini golf, and tennis courts. Visit early on summer mornings to avoid crowds at the play areas, or come at dusk when the park's lighting creates a magical atmosphere.

Maggie Daley Park

Chicago Shakespeare Theater

Located near Navy Pier, the world-class Chicago Shakespeare Theatre presents quality productions in an intimate setting. The main theater's design means no seat is more than 30 feet from the action. Along with Shakespeare, the theater presents musicals, international productions, and family programming. The TheaterBox space hosts experimental works and visiting companies. Arrive early to explore the lobby exhibits about current productions.

Chicago Shakespeare Theater

Chicago Children's Museum

Three floors of hands-on exhibits at the Chicago Children’s Museum encourage learning through play. The Tinkering Lab lets kids experiment with real tools and materials. The Dinosaur Expedition recreates a real Chicago fossil dig site. Water City teaches about the Great Lakes ecosystem, and the Treehouse Trails offers safe exploration for toddlers. Visit on Thursday evenings for free admission, or first Sundays for free access for children 15 and under. Morning visits tend to be quieter, especially on weekdays.

Chicago Children's Museum

Logan Square

The historic boulevard district, Logan Square, is one of Chicago's most vibrant neighborhoods. The Logan Theatre, restored to its 1915 glory, shows indie films and hosts special events. The Logan Square Farmers Market operates year-round, moving indoors during winter months. The restored graystones and boulevard system earned Logan Square a spot on the National Register of Historic Places. Visit during the summer to experience the Logan Square Arts Festival.

Logan Square

Pilsen

Pilsen is a Lower West Side neighborhood that showcases Chicago's Mexican-American heritage with vibrant murals, galleries, and restaurants. Visitors can visit The National Museum of Mexican Art for free to see the rotating exhibits that celebrate Mexican culture. On 18th Street, you’ll find authentic taquerias, vintage shops, and independent art spaces. Visit during the annual Pilsen Food & Wine Festival to sample the area's best cuisine, or join a mural walking tour to learn about the neighborhood's public art.

Pilsen

Lincoln Park Zoo

The Lincoln Park Zoo is one of North America's oldest free zoos and is home to over 200 species of animals. The Farm-in-the-Zoo lets children connect with domestic animals. Visit during morning feeding times for the most active animals, or plan your visit around seasonal events like ZooLights and beer festivals. The zoo's free admission policy makes it easy to stop in for brief visits anytime.

Lincoln Park Zoo

The Second City

Legendary comedy theater, The Second City, has launched countless stars including Bill Murray, Tina Fey, and Stephen Colbert since opening in 1959. The Mainstage and e.t.c. theaters present original sketch comedy and improv shows nightly, while the Training Center offers classes for aspiring comedians. Be sure to catch a Mainstage show Thursday through Saturday when the most seasoned performers take the stage.

The Second City

Chicago Boat Tours

Boat tours are a unique way to see the city skyline from Lake Michigan and the Chicago River. You’ll find a variety of boat tours and cruises at Navy Pier. Sightseeing cruises glide past iconic buildings. Dining cruises pair stunning views with upscale meals. Thrill-seekers can opt for high-speed rides that zip across Lake Michigan, and families can find more relaxed tours that are fun for everyone. Book morning cruises for calmer waters and smaller crowds, or choose a sunset cruise to watch the city lights come alive.

Chicago Boat Tours

Plan Your Chicago Adventure

Whether you're visiting for a weekend or a permanent resident, you’ll never run out of things to do and places to explore in Chicago. Don’t forget to start your Windy City adventure at 360 CHICAGO, where you can experience unique views of the city along with the excitement of TILT and enjoy drinks at the CloudBar.

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Chicago is your ideal outdoor playground to celebrate the changing seasons as winter’s chill fades into the warmth of spring. Whether you're a local looking to rediscover your city or a visitor eager to explore, there are an abundance of things to do in Chicago in spring.

Go Kayaking

Find your scene—kayaking scene, that is. Choose from a diverse range of settings to enjoy a guided kayak tour or rent your own. Kayak tours in Chicago are a popular and unique way to see some of the city’s famous architecture. Glide over the water of the Chicago River and view the infamous “Corn Cob” towers, sprawling Merchandise Mart and other well-known sites. Kayaking on Lake Michigan also offers premium city vistas with the added benefit of being able to cruise between beaches (think beachside picnic!). Or journey outside the Windy City to paddle along the peaceful lagoons on the Skokie River where you might see deer and even bald eagles.

Kayaking is one of the best things to do in Chicago in Spring

Take an Architecture Boat Tour

If you wish to see the city from the water but don’t want to paddle your way along the waterways, then a Chicago architecture boat tour is for you! Journey through all three branches of the Chicago River with Shoreline Sightseeing and enjoy amazing views of more than 40 Chicago landmarks. This 60-minute architecture boat tour is the perfect way to dip into Chicago’s fascinating architectural history as their knowledgeable guides reveal the captivating stories behind the legendary builds.

Boat tour in the Chicago spring

Stop & Smell the Flowers

Spring breathes new life into the landscapes in and around Chicago. Although there are numerous flowers blooming throughout the city, four locations are well-known for their springtime blooms and are worth a visit. The Magnificent Mile tulips add a fresh wave of color to this popular area as thousands of flowers bloom along Michigan Avenue. The Lincoln Park Conservatory and the Garfield Park Conservatory both offer a dazzling array of flora to discover and are a wonderful way to spend time during springtime showers. Visiting Jackson Park at the end of spring is a must-do experience to see the park’s shoreline colored pink by the nearly two hundred cherry trees in bloom.

Flowers during the Chicago spring

Lean into Springtime on TILT

To kick off your spring adventures, enjoy a bird’s eye view of the city at 360 CHICAGO, located on the 94th floor of the former John Hancock Building. Here you can step into a one-of-a-kind thrill ride on TILT, which slowly leans you outward at a 30-degree angle with nothing to block your face-first view of Chicago's skyline. Then you can toast the warmer days with a new favorite cocktail at CloudBar–Chicago’s highest bar!

TILT at 360 CHICAGO

Catch a Ballgame

You can’t talk about spring in Chicago without mentioning baseball. Chicago holds the distinction of being the only city to have had more than one MLB team every year since the league’s founding in 1901. Will you cheer on the White Sox or the Cubs–or perhaps both? Get your tickets, don your jersey, and join locals at either Wrigley Field or Rate Field for an unforgettable day at the ballpark.

Wrigley Field in spring in Chicago

Celebrate St. Patrick’s Day

If you’re planning on visiting Chicago in March, consider arranging your travel plans around Chicago’s St. Patrick’s Day celebration. The city’s St. Patrick’s Day Parade is one of the largest in the country and turns Columbus Drive into a magnet for all things green with festive attendees and colorful floats. In honor of the day, the Chicago River is dyed green, which makes for an even more memorable boat tour! There are other parades in addition to the main one down Columbus Drive. There are also numerous opportunities to toast St. Patrick in bars and restaurants across the city.

St. Patrick's Day in Chicago in spring

Stroll (or Run or Bike) the Lakefront Trail

Few things feel as wonderful as being outside on a warm spring day, especially after a long and cold winter. As the weather brightens, the foot traffic increases along the popular Lakefront Trail, which is an 18.5-mile-long paved trail that links beaches and four major parks along Lake Michigan’s western shore. Enjoy a walk to one of the parks and/or beaches, or bike the length of the trail for an exhilarating day along the shoreline. The Navy Pier and the Museum of Science and Industry are just two attractions that are easily accessed from the trail if you're looking for even more things to do in Chicago in the spring.

Stroll on the Lakefront Trail

Experience Art on the Mart

Since its founding in 2018, Art on the Mart has been a pioneer in digital art. Beginning in the spring, this cutting-edge art platform transforms the country’s largest privately held commercial building—The Mart—into its digital canvas. People come from all over to sit at the Riverwalk and see contemporary moving-image art projected onto the 2.5-acre facade. Work by national and international artists is featured during the event.

Experience Art on the Mart

Attend Expo Chicago

In addition to experiencing Art on the Mart, art lovers should take the opportunity to attend EXPO CHICAGO—an event that highlights the local contemporary art community alongside internationally renowned artists. Located at the Navy Pier, the expo offers multiple galleries and ambitious installations to explore, in addition to panels and forums.

Expo Chicago in spring

Visit Lincoln Park Zoo

One of the oldest zoos in North America, the Lincoln Park Zoo is home to over 1,000 animals representing nearly 200 species. Spend a sunny Chicago spring afternoon visiting the polar bears, penguins, gorillas, and more as you stroll through the zoo’s 35 acres that have been thoughtfully landscaped, providing an inviting backdrop to explore. This zoo is also one of the few in the United States that’s completely free to visit!

Lincoln Park Zoo

Explore Millennium Park

If you’ve scrolled through pictures of Chicago, you’ve most likely seen images of the Cloud Gate statue (nicknamed “The Bean”). The famous structure is located in Millennium Park, along with other popular attractions that are worth visiting on a pleasant spring day. The award-winning Lurie Garden features native perennials and bulbs that attract a wide variety of birds. Kids can tackle climbing walls, suspension bridges, and tube slides at Maggie Daley Park, along with a mini golf course and roller skating area. The larger park is also home to restaurants and art exhibits. Be sure to check out their calendar for upcoming events!

Explore Millennium Park in Chicago spring

See the Tulip Fields

No words can properly prepare you for what it’s like to wander among what feels like an endless sea of tulips in full bloom. But thankfully, you can experience this awe-inspiring sight for yourself at Richardson Farm where more than 900,000 bulbs are planted, in addition to tens of thousands of daffodils, for your viewing pleasure. Visit their website to check on the timing for the upcoming season, but typically the flowers are in bloom from mid-April to mid-May.

Tulip fields during the Chicago spring

From the blooming gardens and sparkling lakefront to exciting outdoor activities and the thrilling TILT ride, there are just so many things to do in Chicago in Spring - there's something for everyone. Start planning your spring vacation in Chicago today!

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For those looking for adventures in Chicago, the Windy City has so much more to offer than deep-dish pizza and architecture tours. Adrenaline seekers of all kinds will have no trouble finding an experience to get their hearts pumping! And this curated list features some of the most adventurous things to do in Chicago!

Soar above the skyscrapers, race across the water, or get competitive with your friends on your Windy City adventure.

TILT at 360 CHICAGO

Start your Chicago adventures 1,030 feet above the Magnificent Mile at TILT. This one-of-a-kind thrill ride slowly tilts you outward at a 30-degree angle with nothing to block your face-first view of Chicago's skyline. There’s nothing like the rush (or the views) you’ll get when you’re looking down at the city from the 94th floor.

TILT at 360 Chicago, Chicago adventures

Speedboat Tours

Ditch the leisurely stroll along Navy Pier and head out for a thrilling speedboat tour with Seadog Cruises. Choose from several available tours, including the Extreme Thrill Rides tour that zips across Lake Michigan at up to 45 mph. Tours are available daily throughout the warmer months. Just be sure to pack some extra clothes in case things get a little wet!

Speedboat tours around downtown Chicago
Photo credit: navypier.org

Rock Climbing

Challenge yourself to a climb year-round at one of Chicago’s many climbing gyms. In the winter, find a gym that works for your skill level and location with a quick search for nearby climbing gyms. In the summer months, check out the Climbing Wall at Maggie Daley Park. The unique bouldering and climbing structures at the park were custom-designed for all skill levels to enjoy.

Rock climbing in Chicago

Kayaking

Go on an urban paddling adventure designed by Chicago locals with Urban Kayaks. You’ll explore the city from a totally different perspective with guided tours and fully-equipped rentals. Add even more excitement to your water-front experience when you book a sunset or twilight tour. All skill levels are welcome to choose between lakefront or riverwalk locations during warmer months.

Kayaking in downtown Chicago

Helicopter Tours

Adventurous couples and small groups can choose to tour the skyline from above with Fly Heli in Chicago. Choose from a variety of daytime flights for a bird’s-eye view of the city and Lake Michigan, or hop on a nighttime tour to see the city lights. Be sure to book the Chicago Christmas Lights Tour during the Christmas season, or schedule the Marry Me Helicopter Experience for an unforgettable proposal!

Helicopter tours in Chicago

The Forge

The Forge: Lemont Quarries was voted one of the one of the 10 best aerial adventure parks in the United States and is located just outside Chicago in Lemont, IL. The 300-acre park includes ziplines, climbing walls, and ropes courses. Plan an adventurous day out with the whole family at The Forge, where you’ll find activities for all ages and skill levels

The Forge is full of adventurous things to do in Chicago
Photo Credit: WhirlyBall

Whirlyball

What exciting game combines elements of bumper cars, lacrosse, and basketball to create one of Chicago's most unique indoor adventures? Whirlyball, of course! This fast-paced team sport will get your adrenaline pumping and keep you laughing the whole time. Enjoy delicious food and drinks at the on-site restaurant while you’re waiting for your adventure to begin.

The one of a kind Whirlyball in Chicago

Ice Skating

During winter months, take your Chicago adventure to the ice! Book some time on one of the many outdoor and indoor rinks in the city, or challenge yourself on the quarter-mile skating ribbon at Maggie Daley Park. You’ll navigate curves and changes in elevation on this winding, frozen path. Skate rentals are available on-site. Be sure to book your skating time ahead for this popular winter adventure. 

Ice skating in Chicago

Rage Rooms

Book the ultimate stress-relieving adventure at the Purge Rage Rooms at Kanya Lounge. Safely smash everything from bottles to printers in controlled demolition zones. You’ll be sure to get your adrenaline fix while letting off some steam in one of the three custom-made rage rooms. 

Rage rooms in Chicago
Photo credit: kanyalounge.com

Jet Skiing

During the summer months, rent a jet ski from Jet Ski Chicago and zoom across Lake Michigan for an extra dose of adrenaline. Race along the shoreline and see views of Chicago's skyline from the water. Drivers must be 18 years old and up, but children that are at least 42 inches tall can ride as passengers. 

Jet skiing in Chicago

Skydiving

Extreme thrill-seekers looking for one of the most adventurous things to do in Chicago can take the ultimate leap from 13,500 feet with Skydive Chicago in nearby Ottawa. On clear days, you’ll be able to spot the Chicago skyline during your jump while experiencing the pure adrenaline rush of a freefall. First-time skydivers will receive thorough training before being securely harnessed to an instructor for an unforgettable adventure in the skies over Illinois.

Skydiving is one of the best adventurous things to do in Chicago

Altitude Trampoline Park

Adventure seekers of all ages can bounce, flip, and soar at Altitude Trampoline Park. Test your trapeze skills over a soft foam pit, challenge friends to extreme dodgeball, or balance your way across the log roll. Be sure to check out special events like glow nights, or invite your friends to join you for a fun and adventurous birthday party. 

Altitude Trampoline Park is one of many adventurous things to do in Chicago

Axe Throwing

Get your adrenaline pumping and compete with your friends at Bad Axe Throwing in the West Loop. Trained axe coaches will teach proper technique for a fun and safe adventure. Walk-ins are welcome, but it’s a good idea to book a lane in advance, especially on weekends. Food and drinks are available on-site. 

Axe throwing in Chicago

Escape Rooms

Put your problem-solving skills to the test under pressure at the Chicago Escape Room Adventures. You and your friends will be trapped in themed rooms where you'll need to solve puzzles and decode clues in order to escape. Coordinate a prison break or pull of a heist before time runs out!

Escape Rooms in Chicago

Get your heart racing and start planning your next Chicago adventures now! Book your tickets to experience TILT at 360 CHICAGO and get ready for an unforgettable adrenaline rush. 

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There are so many things to do for date night in Chicago that it can be tough to narrow your choices. Even though the Windy City is full of unique experiences and fun activities, you might find yourself planning the usual dinner and a movie simply because it’s easy.

If you’ve fallen into the trap of boring date nights, use this list to inspire fun date ideas! You’ll find activities that are great for a first date, romantic spots for an anniversary dinner, and out-of-the-box ideas for your next unforgettable Chicago date night!

Date Ideas in Chicago 

1. The Second City

The Second City hosts improv comedy shows in several locations so there is always something fun to choose from. Interactive shows take the pressure off first dates with lots of chances to break the ice and laugh together. Choose from a variety of improv, stand up, and sketch comedy shows. Just remember not to sit near the front unless you're both open to becoming part of the show!

2. AIRE Ancient Baths

For one of the most romantic anniversary date ideas in Chicago, book a session at AIRE Ancient Baths in River West. This restored factory houses multiple thermal baths that are modeled after ancient Roman, Greek, and Ottoman bathing experiences. Share a peaceful afternoon moving between the various pools and relaxation areas. Candlelight, luxurious decor, and historic architecture create a memorable setting for couples seeking something beyond the ordinary.
Photo credit: https://beaire.com/

Photo credit: https://beaire.com/


3. Cooking Classes at The Chopping Block

Turn up the heat on date night by learning to make something delicious together. The Chopping Block offers both hands-on cooking classes and virtual demonstrations for all skill levels, from pasta-making to sushi rolling. Working side by side in the kitchen creates plenty of opportunities for conversation, and you'll leave with new skills you can use again during future date nights at home!

4. Zanies Comedy Club

If you’re looking for a Chicago date night idea on a week night, Zanies Comedy Club in Old Town hosts performances every night of the week. Established stand-up comedians and rising stars have been performing at Zanies since 1978. Make reservations in advance and arrive early to snag good seats, although the small venue size means there's rarely a bad view.

5. Field Museum

Plan an adventure to explore dinosaurs and ancient civilizations together at The Field Museum. Take advantage of free admission days for a budget-friendly, daytime date option. You’ll enjoy learning new things together, and the museum's grand architecture and quiet spaces allow for plenty of time for conversation as you explore. 

6. Cindy's Rooftop

Special occasions, romantic evenings, and anniversary dates in Chicago are the time to visit stunning locations you wouldn’t go every day, like a rooftop overlooking Millennium Park. Cindy’s is a glass-enclosed rooftop restaurant and bar with gorgeous views of the city skyline and Lake Michigan. Reservations are recommended, especially during peak hours and weekends.

Photo credit: https://www.cindysrooftop.com/

7. Chicago Food Tours

Plan a special date for the foodie in your life with Chicago Food Tours. Choose from several tours that explore different neighborhoods and cultural cuisines. Tours typically include 5-6 stops, mixing well-known spots with hidden gems. You’ll get to experience multiple restaurants in one evening while keeping the conversation flowing naturally.
 

8. Swan Boats at Humboldt Park

During warmer months, paddle around the lake in Humboldt Park’s iconic Swan Boats! Consider packing a picnic to enjoy on the shore before or after your boat ride. If being on the water isn’t your thing, rent bikes to explore the beautiful gardens and architecture of the area. It’s an Instagram-worthy date location for couples who love a good selfie. 

9. Chicago Botanic Garden

Plan a Chicago date day at Chicago Botanic Garden or Garfield Park Conservatory and stroll through nature together! Taking a walk among the beautiful seasonal gardens and tropical greenhouses is a romantic way to spend an afternoon. Visits to the Garfield Park Conservatory are free year-round for Chicago residents.
 

10. The Riverwalk

Taking a stroll along the riverwalk is a fun Chicago date idea for couples who enjoy staying active. Take a long, meandering daytime walk together, or use the riverwalk as the starting point for a night of tasty food and drinks. You’ll enjoy the fresh air and chance to stretch your legs as you walk between various riverfront locations. 

11. Art Institute of Chicago

Turn your visit to the Art Institute of Chicago into a fun and engaging date by challenging each other to find your favorite pieces in each gallery. You’ll find city views and contemporary art right around the corner from historical artifacts and architecture from around the world. Be sure to check the upcoming event schedule for special exhibits and programs when you plan your next Chicago date night!

12. Lincoln Park Zoo

The Lincoln Park Zoo is always free to enter and is full of year-round date possibilities. Summer evenings bring special adults-only events with cocktails and animal encounters, while winter transforms the zoo into a magical light display during ZooLights. Time your visit around animal feeding times for extra entertainment. 

13. 360 CHICAGO

If you're looking for truly unforgettable date night ideas in Chicago, plan a special outing a thousand feet above the Magnificent Mile at 360 CHICAGO. Share panoramic views of the city and Lake Michigan from the 94th floor observation deck before experiencing TILT, the ride that leans you face-first above Chicago from 1,030 feet in the air! Finish the date at CloudBar with craft cocktails and romantic sunset views from the observation deck.360 CHICAGO

14. Montrose Beach

Many fun dates in Chicago start at the beach! Montrose Beach is a popular spot for both active dates on the water and relaxing dates on the sand. You’ll find kayak and volleyball rentals, food stands for tasty treats, and a dog-friendly area for couples who want to bring their furry friends along. In the spring and fall, take a walk along the natural areas to see visiting migratory birds.
Montrose Beach 

15. Steppenwolf Theatre

Steppenwolf Theater is a community-supported ensemble theater with a variety of year-round shows playing Tuesday-Saturdays. Stop at a nearby restaurant or arrive early for a drink from one of the several in-house bars. It’s the perfect date night for local couples looking to support the arts and enjoy a night of theater together. Steppenwolf Theatre

16. The Aviary

The Aviary takes going out for a night of drinks to a whole new level with their signature dining and cocktail experiences. Choose a cocktail progression for drinks only, or make a reservation for a 5 or 7 course meal that engages all your senses. For a more intimate experience, head downstairs and discover The Office, a speakeasy-style bar below the main dining area. 
Photo credit: theaviary.com

The Aviary

Photo credit: theaviary.com

17. Live Music at The Empty Bottle

The Empty Bottle is a small Chicago music venue with a full bar. You can catch up-and-coming bands with shows most nights of the week. The casual atmosphere, affordable tickets, tasty pizza, and live performances make it a popular spot for first dates and regularly-scheduled date nights alike. 

Live Music at The Empty Bottle

Photo credit: emptybottle.com

18. The Dawson

The Dawson is a restaurant and bar with a charming outdoor courtyard and several beautiful indoor spaces. The historic building was built in 1888 and renovated in 2013. Be sure to reserve a spot ahead of time since it’s also a popular space for private events and parties. 

The Dawson restaurant and bar

Photo credit: the-dawson.com

19. Chicago Magic Lounge

Experience close-up magic in the speakeasy-style Chicago Magic Lounge, hidden behind a laundromat facade. Watch impressive slight-of-hand magic at your table while you eat and enjoy the main stage shows performed by the finest Chicago magicians. Purchase tickets ahead for a romantic date night or special-occassion celebration at this surprisingly sophisticated lounge.Chicago Magic Lounge

20. Music Box Theater 

Upgrade your movie night at the historic Music Box Theater, open since 1929. Catch independent films, foreign releases, or cult classics during their midnight screenings. Check the schedule for special events like sing-alongs and director Q&As. The Music Box Lounge + Garden is open to the public and has a rotating menu of cinema-themed cocktails, an extensive collection of VHS films to browse, and board games to play together.

Music Box Theater 

Photo credit: musicboxtheatre.com

21. Revolution Brewing 

Beer lovers can plan a fun date night in Chicago at Revolution Brewing, Illinois’ largest craft brewery. Enjoy food and locally-brewed beers in the Brewpub + Kitchen, or schedule a tour and tasting at the Brewery + Taproom. You’ll find a wide selection of delicious brews at either location.

Revolution Brewing 

Photocredit: https://revbrew.com/

22. Chicago River Boat Architecture Tours

Plan a unique date that both locals and visitors will enjoy with Chicago River Boat Architecture Tours. All tours will take you on an informative and engaging journey down the Chicago River where you’ll learn about the city’s iconic architecture. The Cocktail Tour and Navy Pier Fireworks Cruise are especially fun date ideas for couples looking for something out of the ordinary.Chicago River Boat Architecture Tours

23. Avondale Bowl

Avondale Bowl is a beautifully restored 1930s bowling alley with a cocktail bar and live music on weekends that make it a lively, fun date spot. You’ll share the experience of vintage gaming in a smaller space that’s calmer and quieter than the typical bowling alley. Make sure to book reservations ahead of time since there are limited lanes.
Avondale Bowl

24. Penguin Foot Pottery

Get your hands dirty together and learn something new at Penguin Foot Pottery. You’ll learn basic techniques and create pieces to take home during one-off pottery workshops. Hands-on activities like this one are fun for early dates or established couples looking to learn something new. Ongoing classes are also available, which works out well for couples who enjoy shared hobbies.

25. City Winery Chicago

Book a guided tour of the winery, see a live show, or enjoy dinner and drinks at City Winery Chicago. Indulge in a wine flight in the restaurant or book tickets to live shows. Make sure to book your date night tickets ahead of time for winery tours and shows for this popular date night spot.
City Winery Chicago

26. Take a Bike Tour

Bike tours are a fun Chicago date idea for active couples who want to get to know more of the city and spend time outdoors. Explore together on two wheels with a personalized, guided tour from Chicago Bike Adventures, or join a guided neighborhood food tour with Bobby’s Bike Hike Chicago.

Take a Bike Tour

Photo credit: bobbysbikehike.com

27. Chicago Glass Collective

Create something beautiful together on your next date at a Chicago Glass Collective workshop. Learn basic glass fusing techniques while making custom pieces like small dishes or holiday ornaments. One-day workshops are open to all skill levels, and couples looking to plan regular date nights can sign up for ongoing classes together.

28. Bad Axe Throwing 

Get ready for some friendly competition on your next date night at Bad Axe Throwing in the West Loop. Trained axe coaches teach proper technique for a safe and fun experience. Walk-ins are welcome, but it’s a good idea to book a lane in advance, especially for weekend dates. Food and drinks are available for those who don’t want to spend their whole night throwing axes. Bad Axe Throwing 

29. Chicago Ghost Tours

Add some spine-tingling excitement to your evening with a walking tour of Chicago's most haunted locations. Chicago Ghost Tours include fascinating historical stories along with spooky legends as you visit haunted houses, cemeteries, and more. What better way to give yourselves a chance to hold on tight to each other’s hands? 

Chicago Ghost Tours

Photo credit: ghostcitytours.com

30. Take a Dance Class 

Get close and learn something new together with couples dance lessons from Arthur Murray Dance Centers. Take a one-time class or sign up for ongoing lessons together. Either way, dance lessons will make date night fun and give you the chance to get out of your comfort zone.
Dance Class in Chicago
In Chicago, there are endless possibilities for creating memorable moments together, whether you’re planning a first date, regular date nights, or special trips and anniversary dates. 

Ready to start planning your next date night in Chicago? Don’t forget to book your visit to 360 CHICAGO, and check out our blog for ideas on even more things to do in the Windy City!

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Winter in Chicago can bring harsh winds and freezing temperatures, but locals and tourists can still find plenty of activities to enjoy. With just a bit of planning and preparation, people of all ages can have fun (and stay warm) during the Windy City’s most frigid months. Here are some of the best things to do in Chicago in the winter.

Visiting Chicago in the Winter

Before you plan your visit, make sure you prepare for the cold! December, January, and February are the coldest months, when the temperatures are below freezing most days. Snowfall is also common, so be sure to plan extra time for getting around the city safely.

Stay warm by packing plenty of heavy layers. A good winter coat, gloves, hat, and insulated boots will help you enjoy outdoor activities and keep you warm as you travel. Despite the cold, there are plenty of ways to enjoy yourself with winter activities in Chicago.

Things to Do in Winter in Chicago

1. Sledding

Even when there’s not a lot of snow in the forecast, the hill by Soldier Field stays ready for sledding during winter months. If there’s not enough natural snow, the hill is covered in artificial fluff! Only plastic sleds are allowed, and you’ll want to call ahead to make sure the hill is open during your visit.

Sledding in chicago in winter

2. Ice Skating

Ice skating is a popular winter activity in Chicago, and there are several seasonal outdoor rinks to choose from. Each rink will have its own schedule and will rely on the weather, so be sure to check ahead of time before you head to the rink.

  • Skating at the McCormick Tribune Ice Rink in Millenium Park is free (skate rentals available), but reservations are required.
  • Reserve your ticket to skate down the Ice Skating Ribbon, a quarter-mile skating path in Maggie Daley Park.
  • Check ahead for open skating dates and special events at the Midway Plaisance Ice Rink.
  • For a different view of the city, skate four floors off the ground at The Sky Rink located on the rooftop of The Peninsula Hotel in downtown Chicago. Check ahead for reservations, as the Sky Rink is only open on select winter dates.

Ice skating in Chicago in winter

3. Outdoor Dining

The Windy City knows how to provide comfortable outdoor dining in any weather. Check out one of the many heated outdoor eating spots in the city for a delicious winter meal. Many Chicago restaurants get creative with greenhouses, igloos, and fire pits to keep their outdoor dining spaces open all year round.

Outdoor dining in Chicago in winter

4. The Gwen

Combine winter sports with tasty cocktails at The Gwen during winter months. The rooftop terrace is transformed into a curling rink when the weather gets cold, and rink reservations come with a drink to keep you warm while you play.

The Gwen in Chicago in winter

5. 360 CHICAGO

Discover the best views of Chicago while staying warm indoors at the 360 CHICAGO Observation Deck. Standing 1,030 feet above the Magnificent Mile, you’ll have the chance to see how magical the Chicago skyline and Lake Michigan are when they’re covered in snow.

While you’re there, you won’t want to miss TILT, the only ride in Chicago that angles you out over the city for a face-first view from 94 floors up! You don’t have to be outside to get your adrenaline moving.

After all those snowy views, warm up at CloudBar. All ages are welcome, so grab a snack and a hot cocoa before heading back out into the winter air. Or stick around for an evening of cozy cocktails and breathtaking views of the night skyline.

360 CHICAGO in Chicago in winter

6. Snowshoeing

Northerly Island Park is home to all kinds of outdoor activities, including snowshoeing in the winter. You can head out to the peninsula for a snowy walk anytime the snow is deep enough, but be sure to check out the free Polar Adventure Days that happen every winter. You’ll be able to rent snowshoes, see live animals, and check out winter-themed art.

Snowshoeing in Chicago in winter

7. Museums

Many Chicago museums offer free admission on certain days during the winter, so be sure to plan your visits accordingly.

Museums in Chicago in winter

8. Lincoln Park Zoo

Bundle up to see the polar bears, snow monkeys, and more cold-weather animals enjoying themselves during the winter at the Lincoln Park Zoo. You’ll also be able to warm up in the many buildings that house animals from warmer climates. If you’re visiting during the holidays, you won’t want to miss ZooLights, when the Zoo is turned into a twinkling wonderland of holiday lights.

Lincoln Park Zoo in Chicago in winter

9. Indoor Gardens

Stay warm and connect with nature year-round at one of Chicago’s indoor gardens.

  • The Garfield Park Conservatory is one of the largest conservatories in the country, with eight indoor display gardens. Tickets are free year-round for Chicago residents, while visitors to the city will pay a small fee during winter months. Reservations are required for all visits.

    The Lincoln Park Conservatory is housed in a beautiful Victorian greenhouse built in the 1800s. Entry is free, with reservations highly recommended.

Indoor Garden in Chicago in winter

10. Christkindlmarket

The Christkindlmarket is a German-style outdoor Christmas Market with free admission. You’ll be able to shop for unique holiday gifts from vendors, sip hot cider and spiced wine, and enjoy the festive decorations. Be sure to check the calendar for special events and open dates, and don’t forget to bundle up!

Christkindlmarket in Chicago in winter

Plan Your Winter Visit

Don’t let the cold winter weather keep you from a visit to Chicago. There are plenty of opportunities for fun year-round! Stay cozy indoors or layer up for outdoor winter adventures. You can enjoy the coldest season of the year no matter what type of activities you prefer with all the fun things to do in Chicago in winter.

Experience the best of both worlds at 360 CHICAGO, where you can stay warm while enjoying panoramic views of the chilly city. Book your tickets now for your winter vacation (don’t forget to grab your coat!)

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If you're planning a trip to Chicago and want to add something interesting to your itinerary, consider visiting the CloudWalk at 360 CHICAGO on the 94th floor of the 875 North Michigan Avenue building (formerly the John Hancock Center). This observation deck features a new mural by local artist Katie Chung, making it an exciting spot for art lovers and Chicago visitors.

What is CloudWalk?

The Chicago CloudWalk is an outdoor viewing platform at 360 CHICAGO, offering breathtaking panoramic city views from 1,030 feet above Michigan Avenue. As part of a recent extensive renovation, CloudWalk now boasts a site-specific local art area, Locals Only, created by renowned Chicago artist Katie Chung. This mural spans seven windows and includes hand-painted walls and floor, turning the observation deck into an immersive art experience.

Cloudwalk 1

Experience the Vibrant Art

Katie Chung’s mural is a cultural journey through Chicago. Her bold graphics and bright colors, influenced by the traditional Korean color scheme Obangsaek, create a lively and engaging atmosphere. The mural pays homage to her Korean heritage and the diverse neighborhoods that comprise Chicago's social fabric.

Meet the Artist: Katie Chung

Katie Chung is a second-generation Korean-American artist who grew up in Chicago’s Lakeview neighborhood. She graduated with a BFA from the School of the Art Institute of Chicago (SAIC) and is best known for her work in textiles, bookbinding, printmaking, and design. Her deep-rooted connection to Chicago and her Korean heritage are evident in her vibrant, culturally rich artwork.

Chung's Locals Only mural draws inspiration from Chicago’s diverse neighborhoods and iconic landmarks. She beautifully captures the essence of Chicago's multifaceted identity by incorporating elements such as the bungalow homes of Jefferson Park, the entrance gate in Chinatown, the Little Village Arch, and views from the city's famous train lines.

Katie Chung Cloudwalk 260 Chicago 2

A Unique Perspective

CloudWalk offers an unparalleled view of the city’s skyline, allowing visitors to see Chicago from a new angle. This skywalk in Chicago has open-air windows and a high vantage point that provides an exhilarating and serene experience. Imagine soaking in the cityscape while surrounded by a masterpiece of modern art.

Engage with Chicago's Culture

The mural Locals Only is an educational and engaging attraction for tourists and locals alike. It highlights the beauty and significance of Chicago’s neighborhoods, encouraging visitors to explore the city beyond the downtown area. Each vignette in the mural tells a story, making your visit to CloudWalk both informative and inspiring.

Perfect for All Ages

Whether you're an art enthusiast, a history buff, or simply looking for a fun family outing, CloudWalk at 360 CHICAGO has something for everyone. The colorful and interactive nature of Katie Chung's mural will captivate visitors of all ages.

It's your chance to experience the unique blend of art and panoramic views. Visit the Cloudwalk for free with General Admission to 360 CHICAGO. 

Planning a trip to Chicago but only have one day to explore the city? We understand the struggle of wanting to see everything in a limited time. That's why we have put together the ultimate itinerary specially designed for travelers who have just one day in Chicago and want to make the most of their short visit. With this guide, you'll experience the best of what the city offers, from iconic landmarks to delicious food spots. Let's dive into the top things to do in Chicago in just one day. Trust us; you won't want to miss anything on this Chicago one day itinerary!

Stop 1: Start the Day with a Hearty Breakfast

Kick off your exploration of Chicago on the right foot with a delightful breakfast to fuel your adventures. Choose from one of these three restaurants that can satisfy every kind of taste and are located near your next stop.

Wildberry Pancakes & Cafe is renowned for its cozy vibe and extensive breakfast menu that caters to all tastes, making it an ideal spot for satiating your morning.

Another great option is the Goddess and The Baker, a cafe that stands out for its unique coffee blends, juice bar, and an assortment of pastries and breakfast sandwiches that are perfect for those seeking a quick yet fulfilling bite.

For a trip down memory lane in a nostalgic diner setting, check out Lou Mitchells which serves hearty, classic breakfast dishes since 1923 that promise to leave you satisfied.

Conveniently located, these eateries provide a seamless start to your day, ensuring you’re well-nourished and ready to take on all the things to do in Chicago in one day.

Stop 2: Stroll Through the Magnificent Millennium Park

After a fulfilling breakfast, go to downtown Chicago's heart for a refreshing morning stroll through Millennium Park. This iconic park is easily accessible by public transportation, bike, or foot from many downtown locations. As you enter the park, the first landmark to greet you will be Cloud Gate, affectionately known as "The Bean." This massive, mirror-like sculpture reflects the city's skyline and the sky above, offering a unique photo opportunity synonymous with Chicago's creative spirit.

Just a short walk from Cloud Gate, you'll find the Crown Fountain, an interactive art piece that features two 50-foot towers projecting the faces of Chicago citizens, with water playfully spouting from their mouths. It's a refreshing stop, especially on warmer days. Continue exploring the serene Lurie Garden, which offers a peaceful escape with its beautifully landscaped gardens and skyline views.

Adjacent to Millennium Park, Maggie Daley Park contrasts with its adventurous playgrounds, perfect for visitors of all ages. Here, you can enjoy a leisurely walk along winding paths or engage in some of the park's recreational activities.

Starting your day in Millennium Park immerses you in Chicago's artistic and cultural heartbeat and positions you perfectly to explore the rest of the city's downtown attractions.

The Bean in Millennium Park

Stop 3: Visit the Infamous Museum Campus

Your Chicago in one-day adventure wouldn't be complete without a visit to the city's esteemed Museum Campus, a 57-acre park nestled along the sparkling Lake Michigan shoreline that houses three of the city's most renowned institutions: the Field Museum, Adler Planetarium, and Shedd Aquarium. You can get to this iconic cultural destination with a 20-minute train/bus trip, a 6-minute cab ride from your last stop or a scenic walk along the lakefront path from downtown.

At the Field Museum, one of the largest natural history museums in the world, you're invited to explore the wonders of ancient civilizations, marvel at towering dinosaur skeletons, and dive deep into the story of life on our planet. It's a place where history and science come alive in the most engaging ways.

Just steps away is the Adler Planetarium, which offers a gateway to the stars, with captivating exhibits that span the history of space exploration and immersive planetarium shows that transport you across the galaxy. It's a must-visit for anyone fascinated by the mysteries of the universe.

The Shedd Aquarium opens a window into the aquatic world, featuring an extensive collection of marine life from around the globe. From colorful fish to playful dolphins, the Shedd Aquarium provides an up-close look at life beneath the waves.

While it will be challenging to see all three in one day, selecting the one that most aligns with your interests will ensure a memorable and enriching addition to your one-day itinerary in Chicago. Grab a quick snack at the Museum Cafe or hold off till the other stops for lunch on the go at one of many downtown cafes.

The Shedd Aquarium

Stop 4: Discover the Famous Works at the Art Institute of Chicago

Your Chicago one-day itinerary continues with a cultural journey stepping into the halls of the Art Institute of Chicago. This world-renowned museum is located on the edge of Millennium Park and is just a 22-minute ride via transit from the museum campus.

As you approach the museum, the iconic bronze lions guarding its entrance welcome you into a sanctuary of art and history that spans thousands of years and encompasses many cultures. Inside, the Art Institute boasts an extensive collection that includes everything from ancient artifacts to modern masterpieces. Prepare to be mesmerized by the museum's impressive holdings of Impressionist and Post-Impressionist paintings, with works by Van Gogh, Seurat, and Monet taking center stage. Beyond these, the museum offers an eclectic assortment of galleries featuring American art, European armor, textiles, and photography, ensuring that there's something to pique the interest of every visitor.

The Art Institute Chicago

Stop 5: Head to the Chicago Architecture Center

Just a 15-minute walk from stop #4, the Chicago Architecture Center (CAC) is your gateway to understanding the city's long architectural heritage and iconic skyline. Upon arrival, you'll find engaging exhibits that detail the evolution of the city's architecture, from the Great Chicago Fire's aftermath to the birth of the first skyscraper and beyond. Inside, interactive displays and scale models provide insight into the engineering marvels of some of the world’s most famous buildings, all rooted in Chicago's streets.

Chicago Architecture Center

Stop 6: Explore The Magnificent Mile

From the Chicago Architecture Center, head north on Michigan Avenue, a mere stroll away from the iconic stretch known as the Magnificent Mile. This downtown zone offers a vibrant array of shopping, dining, and entertainment options that cater to every taste and budget. Its diverse selection of high-end boutiques, major department stores, and unique local shops invite you to explore and find the perfect memento of your day in Chicago. In addition to the retail experience, this area is dotted with historic landmarks and architectural marvels, providing plenty of photo opportunities as you wander. As you continue your exploration, allow yourself the freedom to walk into any shop that catches your eye, each offering treasures waiting to be discovered.

The Magnificent Mile

Stop 7: Get An Elevated View & More at 360 CHICAGO Observation Deck

One day in Chicago would only be complete with a visit to 360 CHICAGO Observation Deck. This popular destination, located on the Magnificent Mile, is perched high above the city streets and offers visitors a chance to see Chicago from an unparalleled vantage point. Prepare to be amazed by the incredible, sweeping views of the city skyline, Lake Michigan, and, on clear days, far beyond the city limits. The observation deck provides an immersive way to understand the vastness and beauty of the Windy City from 1,030 feet above ground.

But the experience continues beyond just the views. 360 CHICAGO also offers TILT – an exhilarating feature that literally tilts guests over Michigan Avenue for a heart-pounding perspective of the city below. It's a unique attraction that combines a thrill with a view.

After taking in the sights and sensations from TILT, you can unwind and reflect on their sky-high adventure with a visit to CloudBar. This all-ages bar offers a selection of cocktails and mocktails that are as inspired as the panoramic views from the observation deck. Grab a drink and toast to the city's beauty; this stop is a perfect blend of awe-inspiring sights, thrilling experiences, and a touch of leisure, encapsulating the dynamic spirit of Chicago in one memorable destination.

Cloudbar at 360 CHICAGO

Stop 8: Enjoy an Amazing Dinner in Chicago

As your day in Chicago transitions from exploration to relaxation, indulging in dinner will be the next highlight of your itinerary. Without the need to return to your hotel for a wardrobe change, you can choose from several nearby restaurants that offer both convenience and a memorable dining experience. Each restaurant, located near 360 CHICAGO, presents its own unique ambiance and culinary delights, allowing you to select the perfect spot that suits your mood and palate.

Fig & Olive captures the essence of the Mediterranean with its focus on olive oil as a cornerstone ingredient. This upscale eatery offers a menu that emphasizes freshness and flavor, featuring dishes inspired by the coastal regions of Italy, Spain, and France. The inviting, chic atmosphere and a selection of fine wines make this place a superb choice for those seeking a sophisticated dining experience.

Giordano’s serves up its legendary deep-dish pizza for a taste of something quintessentially Chicago. This iconic pizzeria is for anyone looking to sink their teeth into a gooey slice of cheese, rich tomato sauce, and your choice of toppings, all encased in a buttery crust. It’s a hearty and comforting meal that reflects the city’s love affair with this classic dish.

Marisol, nestled within the Museum of Contemporary Art, offers a dining experience with an inventive and approachable menu. The restaurant's bright, airy space is the perfect backdrop for enjoying dishes that showcase local, seasonal ingredients. Whether you’re in the mood for a light, artful salad or a more substantial entree, Marisol provides a refreshing end to a day of sightseeing.

Each dining destination offers an experience that complements your day in Chicago. Whatever you choose, your dinner plans will be delicious and perfect for bringing your Chicago one-day itinerary from day to night.

Restaurants in Chicago

Stop 9: See a Chicago Show in an Iconic Theater

As the evening unfolds, embracing the lively entertainment scene in Chicago is a must, and what better way to do so than by catching a play, musical, live music, or comedy show?

For those looking to laugh until they cry, a short taxi ride will take you to The Laugh Factory, where the comedic talent is as diverse as the city itself, ensuring an evening filled with joy and laughter.

Alternatively, The Chicago Theatre stands as a beacon of the performing arts, its marquee lights beckoning visitors to enjoy performances in an architecturally stunning setting that's as memorable as the shows it hosts.

And for the enthusiasts of soul-stirring blues music, Blue Chicago is about a mile away, offering an intimate setting where you can experience the emotive power of live blues firsthand.

Each of these destinations provides a unique glimpse into the city's cultural tapestry, ensuring your one day in Chicago is as enriching as it is entertaining.

The Chicago Theater

Stop 10: Make a Final Stop to a Rooftop Bar

To cap off your whirlwind day in Chicago with a touch of sophistication, head to one of the city's premier rooftop bars.

Tucked away in the storied Chicago Athletic Association Hotel, Cindy's Rooftop stands as a paragon of cocktail mastery. The bar boasts a stunning glass atrium and breezy open-air areas that offer great views of Millennium Park, the Art Institute, and the glistening expanse of Lake Michigan. Its menu highlights beverages crafted from the finest, seasonally-sourced ingredients, making every visit a celebration of flavor and freshness.

Another stellar option is Roof on the Wit, which is located on the 27th floor of the Wit Hotel near the Chicago Theatre. This innovative rooftop lounge offers a blend of sophisticated cocktail party ambiance and high-energy nightclub vibes. The Roof on the Wit cultivates an exceptional experience no matter the weather, thanks to its retractable roof. The allure of this venue is its distinctive design with fire pits and contemporary seating areas.

Both locations provide a memorable backdrop for the final chapter of your one-day itinerary in Chicago, blending stunning visuals, exceptional drinks, and a taste of the city's vibrant night scene.

Rooftop bar in Chicago

There you have it, one day in Chicago is possible, but next time you visit the windy city, check out more tips, information, and itineraries from our blog to discover even more about this incredible city!

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As summer fades away and the crisp air of autumn rolls in, Chicago transforms into a picturesque wonderland. With the changing leaves and cooler temperatures, fall in Chicago is a magical time to explore the city. There's no shortage of exciting and unforgettable fall activities for those visiting the city or for locals who are planning a fun weekend. From pumpkin patches to cool night activities and seasonal flavors, there's something for everyone. Get ready to immerse yourself in the beauty of the season as we unveil the top activities and sights when you're in Chicago in fall.

Table of Contents

  1. Dive into Arts and Culture
  2. Food & Drink: Seasonal Flavors in Chicago
  3. Enjoy the Changing Colors
  4. Visit A Pumpkin Patch
  5. Enjoy One of Many Chicago Fall Festivals
  6. Head Out for A Big Game
  7. Enjoy Halloween Fun & Frights

1. Dive into Arts and Culture

A. Visit A Museum

Fall in Chicago is brimming with arts and culture, and it's just waiting to be explored. Immerse yourself in the world-renowned collections at the Art Institute of Chicago, where the vibrant hues of fall are matched by the masterpieces inside.

Famous museums, including the Shedd Aquarium, Field Museum,
and the Museum of Science & Industry offer free admission days throughout the season.

For a celestial experience, Adler Planetarium opens its doors for free entry on Wednesdays, letting you gaze into the autumn sky. Embrace the cooler weather with a scenic fall boat tour along Chicago's picturesque waterways, offering a unique perspective of the city's stunning architecture draped in autumn colors.

Adler Planetarium

B. See a Play

The best shows hit the Chicago Fall theaters with plays and live performances for every kind of visitor. Some popular favorites include:

Find more information about what's on in Chicago on the stage here.

Chicago Theater
Photo credit: Chris Smith

C. Watch a Movie Under the Stars

For film enthusiasts, make an outdoor movie part of your Chicago fall activities. ChiTown Movies provides a nostalgic drive-in movie experience featuring blockbusters and classic movies under the stars in the Pilsen neighborhood. Order some food and beverages from the ChiTown Grille to make it a complete night out.

Enjoy an urban open-air cinema experience at the Rooftop Cinema Club at Fulton Market. This venue offers a selection of classic and new films with a starry night sky backdrop. It's a fun blend of cinematic joy with crisp fall evenings.

ChiTown Movies

D. Take a Tour

While exploring the city's vibrant cultural offerings, take in its outdoor architecture and landscapes from a unique vantage point with a fall boat tour. Gliding along the Chicago River provides an unparalleled skyline view, and the fiery fall colors accentuate the city's exceptional landmarks & architecture.

Fall Harbor Cruise in Chicago

E. Other Cultural Events

Art and literature fans should attend the Printers Row Lit Fest, September 7-8th, celebrating literature and the written word. Stroll around in the beautifully lined book stalls under the canopy of fall-colored trees in Lincoln Park, marking a day for self-proclaimed bibliophiles.

Book shopping in Chicago

F. Fall Music Festivals

Get captivated by the musical performances that take center stage during the fall, presenting a spectrum of musical genres embracing the fall rhythm in Chicago.

Riot Fest in Douglas Park, from September 20-22nd, offers a unique opportunity to immerse in Chicago's chaos (in a legal way!) This event merges the raw energy of live alternative rock music (with headliners including Slayer, The Offspring, and Public Enemy) and a vibrant carnival atmosphere complete with festivities and local food and beverage. While the headlining artists draw you in, the enticing carnival rides will make you want to stay!

World Music Festival Chicago from September 20-29th. This annual festival showcases diverse artists from numerous countries. The World Music Festival offers a captivating blend of traditional and contemporary music with free and ticketed performances. Experience the global sounds that this extraordinary event brings to our city.

The Hyde Park Jazz Festival runs September 28- 29th to celebrate the ongoing development of jazz on the south side of Chicago. The event creates opportunities for a diverse group of listeners and creators to support the craft. Attendance is free, but a $10 donation at the entrance is greatly appreciated.

Fall festival in Chicago

2. Food & Drink: Seasonal Flavors in Chicago

As the leaves change color and the air is cool and crisp, Chicago's culinary scene heats up with the season's flavors. Embrace the essence of fall by visiting one of the city's many breweries, such as Revolution Brewing's Tap Room, where seasonal ales and ciders abound. These local establishments often create special drinks that encapsulate the spirit of autumn.

For heartier fare, dive into a slice of deep-dish pizza, a Chicago staple that tastes especially comforting when the temperatures drop. The city's renowned pizzerias, like the famous Lou Malnati's Pizzeria, can be found in multiple locations across the city, regardless of where you are wandering.

To fully immerse yourself in Chicago's culinary diversity in the fall, consider joining a food tour from Chicago Food and City Tours. These guided tours provide a curated experience of the city's best restaurants and hidden gems, letting you savor various seasonal flavors while exploring Chicago's vibrant neighborhoods.

The Chicago fall food and drink festivals are equally delicious. Check out the Lincoln Park Wine Festival, October 4-6th, for a taste of international wines and live music while you stroll through the eclectic art market.

Whether you're a local or a visitor, indulging in these culinary delights across the city is a must-do to experience the authentic taste of fall in Chicago.

Restaurant in Chicago

3. Enjoy the Changing Colors

Chicago transforms into a kaleidoscope of fiery hues during the fall, making it the perfect time to explore the city's natural beauty. Lincoln Park is an expansive green space and neighborhood that has become a vibrant canvas of yellows, oranges, and reds. Wander through the park's winding paths to fully appreciate this seasonal spectacle. The Morton Arboretum, a bit farther from the city's hustle and bustle, offers an immersive fall experience with its vast collection of trees from around the world, each adding its unique color to the autumnal mosaic.

For an exceptional view, ascent to 360 CHICAGO witness the splendor of autumn from every angle. Marvel at the panoramic views of the cityscape, downtown, and parks as the foliage bursts into vibrant hues. Fall is the ideal time to visit this attraction with fewer crowds. Book your 360 CHICAGO ticket today.

For an outdoor experience in the urban parks, visit Promontory Point in Burnham Park, where the striking skyline juxtaposes Lake Michigan's calm backdrop. Stroll through Millennium Park & Lurie Garden, where the iconic Cloud Gate ('The Bean') reflects the changing leaves, providing a stunning photo opportunity in one of the best places to see the changing fall colors.

These locations offer a distinct way to experience the glory of fall in Chicago, inviting locals and visitors alike to revel in the season’s beauty.

360 Chicago

The scenic trails beckon outdoor enthusiasts the opportunity to hike, bike, and run amidst the stunning backdrop of Chicago's fall colors. The Lakefront Trail, an 18-mile stretch along the shores of Lake Michigan, offers panoramic views of the city skyline and vibrant autumn hues. It's perfect for a leisurely bike ride, a brisk run, or a peaceful hike.

For a more nature-immersed experience, the North Branch Trail delivers 16 miles of winding paths through forests and preserves, showcasing the region's rich biodiversity.

The 606, an elevated trail stretching 2.7 miles, provides a unique urban perspective, connecting four neighborhoods with art installations and green spaces.

Lakefront Trail

4. Visit A Pumpkin Patch

Embrace the quintessential fall activity by visiting a pumpkin patch, ideal for families and friends looking for seasonal fun. In the heart of Chicago, JoJo’s Shake Bar transforms an outdoor space into a delightful pop-up pumpkin patch, offering a whimsical backdrop for your autumnal photos along with seasonal treats such as caramel apples, pumpkin pie, apple pie, spiked ciders, and hot chocolate.

Another seasonal option is Jack’s Pumpkin Pop-Up, which opens in September and features many pumpkins and activities like corn mazes and games.

For those willing to venture further into the city, the Night of 1000 Jack-o-Lanterns on the Chicago Botanic Garden grounds illuminates the night with artistically carved pumpkins, creating a mesmerizing spectacle. Carving demonstrations and costumed entertainers also take place.

The Richardson Adventure Farm, known for its epic corn maze, also boasts a sprawling pumpkin patch where you can pick your perfect pumpkin directly from the field.

These seasonal attractions are typically open from September through October, giving you ample opportunity to soak in the fall ambiance, find your ideal pumpkin, and enjoy the flavors of delicious pumpkin goodness.

Pumpkin patch in Chicago

5. Enjoy One of Many Chicago Fall Festivals

Oktoberfest, which takes place from September 27 to 29, brings a taste of Bavarian tradition to the heart of the city, complete with authentic German beers, food, and lively music.

The Lincoln Square Apple Festival, on October 5 and 6, celebrates the harvest season with apple-themed treats, crafts, and family-friendly activities.

Open House Chicago, occurring on October 19 and 20th, invites locals and visitors to explore the city's architectural wonders, offering rare access to historic sites and landmarks not typically open to the public. Each festival provides a unique way to enjoy fall, catering to various tastes and interests.

Festivals in Chicago in the fall

6. Head Out to a Big Game

Autumn in Chicago isn't just about the changing leaves and pumpkin patches; it's also a prime time for sports enthusiasts. The sports scene heats up as the city cools down, offering exciting opportunities to catch a game in person.

Football fans can rally behind the Chicago Bears at Soldier Field, experiencing the thrill of NFL action amidst the crisp fall air. For those who prefer the indoor excitement of basketball, the Chicago Bulls begin their season showcasing high-flying dunks and intense competition at the United Center.

Fall in Chicago also includes the opening season of the Chicago Blackhawks as the players lace up their skates and hit the ice, bringing the fast-paced action of the NHL to fans eager for the puck to drop.

Each game provides a unique way to experience Chicago's sports culture. Whether you're a die-hard sports fanatic or just looking for a lively evening, heading out for a game is a perfect fall activity in Chicago.

Wrigley stadium in Chicago

7. Enjoy Halloween Fun & Frights

Chicago turns into a city of haunts and thrills every Halloween, offering a variety of activities that promise unforgettable spooky fun.

Navy Pier becomes a hub of spooky festivities during Halloween, with its array of costumes, decorations, and events suitable for all ages.

For those who dare, the 13th Floor Haunted House presents a chilling adventure with its intricately designed sets and professional actors that guarantee to spook even the bravest souls.

The Haunted Halsted Halloween Parade is an iconic event where creativity shines. It features elaborate costumes and vibrant floats that parade down Halsted Street, celebrating the community and LGBTQ+ culture.

Arts in the Dark is a unique Halloween parade that transforms the city's streets into an open-air gallery of luminous art, showcasing the city's diverse artistic community.

Each Halloween activity offers a different way to experience the eerie beauty of fall in Chicago, perfect for those looking to enjoy the season with a mix of fun and frights.

Halloween in Chicago

As the vibrant tapestry of autumn unfolds, it's clear that Chicago in the fall is more than just a season; it's an experience brimming with culture, flavor, and adventure. For more tips, insights, and information on making the most of your visit to Chicago, no matter the season, visit our blog. Discover more ways to fall in love with Chicago, and let the Windy City sweep you off your feet this autumn.

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Chicago Skyline

Chicago is a city that truly has it all! Immerse yourself in an array of world-class museums, vibrant comedy clubs, exciting outdoor adventures, and captivating live shows. Perhaps you’d prefer to experience the most exhilarating attractions Chicago has to offer from different perspectives. Catch a baseball game at the iconic Wrigley Field, enjoy family-friendly outdoor fun at Millennium Park, marvel at the stunning skyline from the 360 CHICAGO Observation Deck at sunset, and discover countless other delights.

Explore our curated list of top Chicago attractions that promise to enchant every visitor and make your stay in this mesmerizing city unforgettable.

360 CHICAGO Observation Deck

Family at 360 CHICAGO

Address:

875 N. Michigan Avenue 94th Floor

Hours:

Daily 9 am - 11 pm. The last entry is at 10 pm.

Details:

360 CHICAGO, one of the top attractions in Chicago, is an Observation Deck full of activities located on the 94th floor of the former John Hancock building.

Elevate your Chicago experience with a visit to 360 CHICAGO. This attraction has something for all ages and interests. Enjoy incredible panoramic city views of the city skyline, day or night. For those seeking a thrill, try TILT, one of the world's highest thrill rides. Relax, grab a beverage, and enjoy the views at CloudBar—the all-ages and highest bar in Chicago. View the local art installations, the newly upgraded multimedia concourse, and more. Once you arrive, stay on the Observation Deck as long as you like! Book your 360 CHICAGO ticket today.

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The Magnificent Mile

Magnificent Mile Street View

Address:

North Michigan Avenue

Hours:

Daily 9 am - 10 pm

Details:

The Magnificent Mile is Chicago’s famous and premier commercial district. This mile is home to over 450 retailers (including flagship department stores and boutiques), 275 restaurants, entertainment, and attractions. This area includes famous landmarks such as the Chicago Water Tower and the former John Hancock Center, which features the 360 CHICAGO Observation deck.

Visit the "Mag Mile" for a shopping lover's paradise. You can find the most up-to-date fashion trends, innovative technologies, home goods, and more here. You'll literally find something for everyone in your group, plus lots of incentives and premier savings opportunities.

Want to learn about specific things to do on the Mag Mile? Check out this blog post!

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Shedd Aquarium

Shedd Aquarium

Address:

1200 S DuSable Lake Shore Drive

Hours:

Daily 9 am - 6 pm

Details:

Embark on a mesmerizing underwater journey at Shedd Aquarium, where over 32,000 marine creatures, from beluga whales and bluegills to stingrays, penguins, and sea otters, await your discovery. Check out the 75-minute guided tour highlighting the aquarium's most extraordinary features. Experience the behind-the-scenes magic as you enjoy prime seating for an Animal Spotlight and converse with an animal care manager. You can also explore the exhibits at your own pace with the Shedd Go app, which allows you to navigate the aquarium effortlessly.

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DuSable Black History Museum and Education Center

DuSable Black History Museum and Education Center

Address:

Washington (George) Park, 740 East 56th Place

Hours:

Wed-Sun, 11:00 am - 4:00 pm

Details:

The DuSable Museum of African American History boasts over 15,000 diverse pieces, including paintings, sculptures, prints, and historical memorabilia. It hosts special exhibitions, workshops, and lectures highlighting artists and historical events. Key exhibitions include Freedom: Origin and Journey, honoring lives dedicated to freedom and equality; The Harold Washington Story, chronicling Chicago's first African American mayor; and South Side Stories, showcasing Dr. Margaret T. Burroughs' artistic and activist legacy.

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Check the admission page to see if you qualify for free admission.

The 606

The 606

Address:

1805 N. Ridgeway Avenue

Hours:

Daily 6 am - 11 pm

Details:

The 606 is an abandoned railway transformed into a 2.7-mile elevated park and trail on Chicago's northwest side. Built on an old industrial train line, the 606 features street-level parks, scenic look-out points, an observatory, and public art. Officially named the Bloomingdale Trail, it derives its name from the numbers in Chicago's zip codes. Spanning Wicker Park, Bucktown, Logan Square, and Humboldt Park, the trail is a favorite among walkers, runners, bikers, and families. With bike rentals from Divvy stations and year-round events like community bonfires, the 606 offers something for everyone.

Maggie Daley Park

Maggie Daley Park in Summer

Address:

337 E. Randolph Street

Hours:

Starting at 6 am - 9 pm. Times vary according to the activity.

Details:

During the winter, Maggie Daley Park transforms into a fun winter Ice Skating Ribbon that offers stunning skyline views and a lively ambiance. Lace up your skates (rentals are available) and glide through one of the most unique rink parks. In the summer, the park is the perfect rollerblading destination. The park is brimming with more activities for those who enjoy the outdoors, like a climbing wall, mini golf, tennis, and more. Discover the myriad of attractions at Maggie Daley Park throughout the year.

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Chicago Architecture Center

Chicago Architecture Center

Address:

111 E. Wacker Drive, Suite 1321

Hours:

Sun - Thu, 9 am - 5 pm
Fri & Sat, 9 am - 7 pm

Details:

The Chicago Architecture Center's riverfront location is nearly 10,000 square feet of exhibition space filled with super-sized models and views of iconic skyscrapers. The Center exhibits focus on Chicago’s diverse neighborhoods, housing types, leading architects, and future projects. Among the highlights is the largest scale model of the city, with more than 4,250 miniature buildings, interactive touchscreens, and a cinematic backdrop animating key moments in its history. Alternatively, join a CAC walking tour or River Cruises aboard Chicago’s First Lady. Learn the stories behind the buildings and how the CAC inspires people to discover why design matters.

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Chicago Riverwalk

Chicago Riverwalk

Address:

22 E Wacker Drive

Hours:

Daily 6 am - 11 pm

Details:

The Chicago Riverwalk, located on the south bank of the Chicago River, is a must-visit destination stretching 1.25 miles from Lake Michigan to Lake Street. This award-winning, pedestrian-friendly area offers a rich tapestry of experiences, from intimate coves and breezy cafes to wineries and bars. Visitors can immerse themselves in public art, monuments, and nearby museums or embark on various water excursions, including boat tours and kayaking. The Chicago Riverwalk provides a picturesque backdrop for those who seek culinary delights or cultural enrichment.

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Things to do on or along the Riverwalk:

Historic Pullman Foundation Visitors Center

Historic Pullman Foundation Visitors Center

Address:

1614 E. 113th Street

Hours:

Thu-Sun, 11 am - 3 pm

Details:

In 1880, George M. Pullman established a model industrial town to bolster his luxury railcar business, creating a unique intersection of history, architecture, railroad innovation, urban planning, labor milestones, and civil rights.

The Historic Pullman Foundation now safeguards these historic buildings, documents, and artifacts, acting as the official friends group of Pullman National Historical Park. Visitors, including history aficionados, national park devotees, train enthusiasts, and curious families, can enjoy captivating tours, exhibits, and events at Chicago's inaugural national park.

Griffin Museum of Science + Industry

Griffin Museum of Science + Industry

Address:

5700 S. DuSable Lake Shore Drive

Hours:

Daily, 9:30 am - 5:30 pm

Details:

Adventure through a multi-sensory experience at the Griffen Museum of Science and Industry! With its award-winning exhibits, the museum promises to captivate every visitor through immersive experiences, giant-screen films, and engaging events. Don’t miss the groundbreaking exhibit 007 Science: Inventing the World of James Bond, which delves into the science and technology behind the film series' legendary gadgets, vehicles, and stunts. Each exhibit at MSI is designed to ignite curiosity and inspire a passion for learning, making it the perfect destination to explore the world's marvels during your cherished time off.

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See exciting new exhibits always on display

Adler Planetarium

Adler Planetarium

Address:

1300 S DuSable Lake Shore Drive

Hours:

Daily 9 am - 4 pm

Details:

The Adler Planetarium is a pioneering institution devoted to the wonders of astronomy and astrophysics since 1930. Perched at the northeastern edge of Northerly Island by Lake Michigan, it is considered America's first planetarium. Its core mission is to ignite curiosity and foster a deeper understanding of the cosmos. The Planetarium includes three state-of-the-art theaters, a series of space science exhibits, and a remarkable collection, including the Gemini 12 space capsule and various antique scientific instruments and printed works.

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Chicago Cultural Center

Chicago Cultural Center

Address:

78 E. Washington Street

Hours:

Daily 10 am - 5 pm

Details:

The Chicago Cultural Center, inaugurated in 1897, spans an entire city block across Michigan Avenue from Millennium Park in the Chicago Loop Neighborhood. This magnificent architectural gem, managed by the Department of Cultural Affairs and Special Events, serves as the city's official reception venue. The Mayor of Chicago has welcomed presidents, royalty, and diplomats here. The center is also accessible to the public, who can admire its grand architecture featuring Tiffany stained glass domes and enjoy over 700 exhibits and humanities programs annually, many of which are entirely free.

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Second City

Second City

Address:

1616 N Wells Street, 2nd Floor

Hours:

Mon-Thu, 10 am - 11 pm
Fri-Sun, 10 am - 12 am

Details:

A visit to Chicago wouldn’t be complete without diving into its iconic comedy scene. Many of America's top comedians launched their careers in the Windy City through improv and sketch comedy. The renowned Second City serves as a breeding ground for some of the biggest stars in the industry. Legendary figures such as John Belushi, Tina Fey, and Steve Carell began their journeys here, leaving an indelible mark on comedy. Attending one of Second City's main stage performances is an absolute must.

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National Museum of Mexican Art

National Museum of Mexican Art

Address:

1852 W. 19th Street

Hours:

Tue-Sun, 10 am - 5 pm

Details:

This sprawling 48,000-square-foot, cutting-edge museum is dedicated to deepening the understanding and appreciation of Mexican art and culture on both sides of the border. The museum boasts an impressive permanent collection of Mexican art, complemented by visual and performing arts programs, top-tier arts education initiatives, and resources for the professional growth of Mexican artists. Check out one of the largest collections of Mexican art in the US (over 22,000 pieces) and cultural programs—including theater, dance, music, and literary events- that celebrate the rich tapestry of Mexican heritage.

Chinatown

Chicago Chinatown

Address:

Cermak Road and Wentworth Avenue

Hours:

24 hours

Details:

Since 1912, this tight-knit community has flourished in Chicago's South Side, spanning Wentworth Avenue and attracting residents and tourists. The neighborhood offers a lively experience with its authentic cuisine, captivating architecture, and numerous shops, cafes, dim sum spots, and teahouses. For a more extensive shopping experience, explore the Chinatown Square outdoor mall. To delve into the rich history, visit the Chinese-American Museum.

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Wrigley Field

Wrigley Field

Address:

1060 W. Addison Street

Hours:

See the game and tour schedule.

Details:

Ignite your passion for sports and history by visiting Wrigley Field, a Chicago treasure steeped in over a century of heritage. Whether you catch a game, stroll among the seats and concession stands, or take a full stadium tour, the experience will be captivating. Every Cubs enthusiast, regardless of age, will delight in standing on the same field graced by legendary players, relaxing in the dugouts, and exploring much more.

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Millennium Park

Millenium Park

Address:

The Loop Community Area

Hours:

Daily, 6 am - 11 pm

Details:

Millennium Park is a must-visit attraction in the heart of downtown Chicago, offering diverse activities and sights. The lakefront campus features the iconic Cloud Gate statue, interactive fountains, serene gardens, free events, public art, skating rinks, rock climbing, and expansive green spaces. Don’t miss the Jay Pritzker Pavilion, where a state-of-the-art sound system mimics indoor theater acoustics. Enjoy events like the Summer Music and Film Series on the Great Lawn and visit Lurie Garden, an award-winning botanical masterpiece that provides a peaceful oasis with native plants year-round.

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Chicago History Museum

Chicago History Museum

Address:

1601 N. Clark Street

Hours:

Tues–Sat, 9:30 am - 4:30 pm
Sun, 12:00 pm - 5:00 pm

Details:

Immerse yourself in the rich tapestry of Chicago's history at the Chicago History Museum. There are many stories to uncover, from the city's sports legacy and political milestones to the iconic Union Stockyards and the infamous Great Chicago Fire. Engage with c exhibitions and dynamic programs within the museum's walls, or experience the city's history firsthand through guided tours and special events. Established in 1856, the museum stands as a beacon of knowledge, inspiration, and civic participation, illuminating Chicago's past, present, and future.

Art Institute of Chicago

Art Institute of Chicago

Address:

111 S Michigan Avenue

Hours:

Thu-Mon, 11 am - 8 pm
Tue-Wed, Closed

Details:

The Art Institute of Chicago is a world-renowned museum boasting one of the largest permanent collections in the United States. This encyclopedic institution collects, preserves, and exhibits works across all mediums, cultures, and historical periods while hosting unique exhibitions. With over 260,000 pieces of artwork, the museum excels in Impressionist and Post-Impressionist art, early 20th-century European pieces, contemporary art, Japanese prints, and photography. The Art Institute also offers about forty special exhibitions annually and daily lectures, tours, and performances.

Lakefront Trail

Lakefront Trail

Address:

From Ardmore Ave. on the north to 71st St. on the south, Chicago

Hours:

Open Daily

Details:

One of the hallmark characteristics of Chicago is its iconic setting along the shores of Lake Michigan, encompassing 26 miles of breathtaking coastline. Integral to this waterfront is the Lakefront Trail, a charming pedestrian route extending over 18 miles. This trail provides awe-inspiring vistas of the lake and the city’s skyline. Throughout the year, it attracts walkers, cyclists, and runners alike. The Lakefront Trail seamlessly links numerous lakefront parks, beaches, museums, neighborhoods, and waterfront dining spots, making it a vibrant artery of urban life.

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The Green Mill

The Green Mill

Address:

4802 N Broadway Avenue

Hours:

Daily 4 pm - 1 am

Details:

Celebrating a centennial milestone, the Green Mill Jazz Club is the city's quintessential jazz venue. With its doors first opening in 1907, this establishment has earned the title of the oldest jazz club in the United States. Once a favored spot for the infamous Al Capone, it exudes the charm and secrecy of Prohibition-era speakeasies. Styled after the 1940s, the club offers live performances every night of the week. Even if jazz isn't your usual scene, the club's history and roster of legendary performers and patrons make it a must-visit. True to its roots, it remains a cash-only bar, just as it was in the 1940s.

The Field Museum

The Field Museum

Address:

1400 S Lakeshore Drive

Hours:

Daily 9 am - 5 pm

Details:

The Field Museum of Natural History is the attraction in Chicago offering a treasure trove of wonders to captivate visitors of all tastes. Since its establishment in 1894, the museum has amassed a staggering collection of over 40 million specimens and artifacts from around the globe. The museum's architecture narrates an extraordinary history. With ever-changing exhibits, there's always something new and exciting to discover.

Navy Pier

Navy Pier

Address:

600 E. Grand Avenue

Hours:

Sun-Thu, 11 am - 9 pm
Fri-Sat, 11 am - 10 pm

Details:

Navy Pier spans 50 picturesque acres along the waterfront, offering an array of dining, exhibitions, shops, and entertainment. Revel in the breathtaking views of Lake Michigan and the Chicago skyline as you ride the 200-foot Ferris wheel, explore the hands-on exhibits at the Chicago Children's Museum, attend a free concert, or embark on a quest to discover art and murals. Thrill-seekers can indulge in exhilarating speedboat tours, while those looking to relax can opt for a serene sightseeing cruise.

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Whatever Chicago Attractions you choose to visit, your visit will be incredible. For more tips and ideas for enjoying Chicago, follow our blog.

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