Let’s be honest; there’s a lot to do in Chicago. So much so that trying to plan a quick trip to Chi-Town can feel overwhelming. But if you're looking to squeeze the most out of your weekend visit, you've landed in the perfect spot. We've crafted the ultimate itinerary for one spectacular weekend in Chicago, designed to hit all the highlights, sprinkle in some hidden gems, and leave you with incredible memories.
You’ll arrive for your much anticipated weekend in Chicago and check into your hotel. So, what next? No matter whether you arrive by car or plane, you’ll need to stretch your legs and shake off that travel fog. The best place to do that is along the 1.25-mile-long Chicago Riverwalk that runs from Lake Michigan to Lake Street. Stroll past illuminated buildings that are architectural icons, by museums, and popular waterfront bars and restaurants. Plus, this must-do pedestrian path winds past the impossible-to-miss Art on THE MART, which is the world’s largest digital art projection with nightly shows from April through December.
Then it’s time to do dinner right on your first night in Chi-Town. That means diving into a cheesy, saucy, delicious deep-dish pizza. Giordano's offers a stuffed pizza experience that's practically a lasagna in pizza form—layers of cheese and toppings generously sandwiched between two crusts, then topped with their signature tomato sauce. Then there's Lou Malnati's, with its buttery, flaky, almost pie-like crust, a robust tomato sauce, and their special "buttercrust" option that's a game-changer.
Top off your first amazing night in Chicago with a nightcap on the 94th floor of the former John Hancock building. Here, you can kick back at CloudBar in 360 CHICAGO with a handcrafted cocktail (try the Hancock Handshake!) and toast views of the cityscape glowing beneath a blanket of stars.
Get ready for a whirlwind (but in a fun way!) day in downtown Chicago. There’s lots of parking around Millennium Park, which is an excellent central location to begin your exploration. But to truly start your day off right, you need the proper fuel to get you going! Enter Stan’s Donuts & Coffee and Hero Coffee Bar.
If you’d like a more savory breakfast, stop by Hero Coffee Bar on your way to the park. Tucked away in a charming alleyway, this coffee bar offers fantastic coffee and a selection of satisfying bagel sandwiches. If you need a sugar boost to get going, then swing by Stan’s Donuts & Coffee at Millennium Park. From classic glazed to their famous Biscoff pocket and delightful seasonal flavors, you can grab a box of their delicious creations and a coffee to enjoy as you stroll toward the dock for your architecture boat tour.
The CAC River Cruise aboard the First Lady is always a crowd pleaser and has won multiple awards. Pro-tip: Book the 9 a.m. sailing for your architecture boat tour. Early birds get the best views (and beat the crowds, trust us). You'll have unobstructed sightlines for those jaw-dropping skyscrapers, stunning bridges, and the winding river. This early slot means prime photo opportunities without a million other phones in your shot.
The angles you’ll capture from the water are simply epic. Every turn offers a new, dramatic perspective of the city's famous skyline, from historic Art Deco marvels to sleek modern giants. With engaging guides who bring the city's stories to life, you'll learn fascinating facts and entertaining anecdotes about how Chicago became an architectural powerhouse.
After your boat tour, stop by the nearby Wabash Arts Corridor. This isn't your typical stuffy museum; it's a "living urban canvas" where large-scale murals, mind-bending installations, and thought-provoking street art from local and international artists are featured on building facades, alleyways, and unexpected corners.
Ready to refuel after a morning of architectural wonders and artistic marvels? Whether you’re just wanting a snack or are hungry enough to eat a cow, here’s two iconic Chicago eats to add to your must-do list: Garrett Popcorn and Billy Goat Tavern.
Hit up Garrett Popcorn Shop for that irresistible aroma and a snack you can munch on throughout the day. Try their famous Garrett Mix that’s a magical blend of savory CheeseCorn and sweet CaramelCrisp. Then, get a taste of history and a whole lot of character at Billy Goat Tavern. Made famous by "Saturday Night Live" with their "Cheezborger, Cheezborger!" skit, this no-frills spot serves up classic, griddle-smashed cheeseburgers (and yes, it's "cheeps" not "fries," and "Coke" not "Pepsi"). It's a quick, delicious, and wonderfully quirky Chicago institution that promises a satisfying and memorable meal.
Next up is a stop at Navy Pier and a ride on the iconic Centennial Wheel. Perched at the end of the pier, this nearly 200-foot-tall Ferris wheel offers unparalleled lake-meets-sky visuals. Step into a comfortable, climate-controlled gondola to be treated to jaw-dropping, 360-degree panoramic views of Lake Michigan and the city skyline.
After getting the lay of the land on the Ferris wheel, head on over to the waterfront to experience the lakeshore for yourself. Recline on one of Chicago's gorgeous beaches, dip your toes in Lake Michigan, build a sandcastle, or simply relax and enjoy the skyline views.
If you’re feeling more adventurous, rent a Divvy bike and hit the 18-mile Lakefront Trail that offers uninterrupted lake views on one side and the cityscape on the other. And if the weather's just right, take your adventure onto the water with a kayak rental.
To close out your day, buy golden-hour tickets at 360 CHICAGO to witness a spectacular sunset. Be sure to reserve your timed entry in advance to snag that perfect golden-hour glow.
After watching the city twinkle to life, enjoy an exhilarating experience on TILT. You'll be securely tilted outwards at a dramatic downward angle, giving you an unparalleled, adrenaline-pumping perspective of the Magnificent Mile far, far below. Lean into the excitement and then unwind at CloudBar with a delicious small-plate dinner. Adults can enjoy local drafts from Chicago's booming craft beer scene, while teens can sip on refreshing mocktails. Don't forget to see the rotating local art exhibits on CloudWalk, located on the outdoor viewing platform.
And while you’re in the area, enjoy a post-deck walk to the Historic Water Tower. It's just a five-minute stroll, and the beautifully lit, gothic tower provides a fantastic opportunity for some stunning night photography.
Savor a leisure Sunday morning with brunch on The Loop. The popular Wildberry Pancakes and Cafe is known for its generous portions and their deep-dish French toast. It's thick, fluffy, and often loaded with decadent toppings. Or, if you're craving a brunch with a side of stunning scenery, Cindy's Rooftop is for you. Located atop the Chicago Athletic Association Hotel, Cindy's serves up views of Millennium Park and Lake Michigan with their brunch menu that features delicious skillet dishes that are perfect for sharing (or not!).
Once your stomach is happily full, feast your eyes on masterpieces at the Art Institute of Chicago.To make the most of your visit at the museum, book your "skip-the-line" tickets online for a Fast Pass experience. Discover one of the world's finest collections of Impressionist art, including iconic works by Monet (don't miss his "Stacks of Wheat" or "Water Lilies"!) and Seurat's mesmerizing "A Sunday on La Grande Jatte" (yes, the one from Ferris Bueller's Day Off!). Then, explore the sleek Modern Wing to see groundbreaking 20th and 21st-century art from giants like Picasso, Chagall, Dalí, Warhol, and more.
Touring Chicago’s art scene wouldn’t be complete without a stop at Millennium Park. Here, you can visit the iconic Bean, officially known as Cloud Gate. This giant, reflective sculpture mirrors the city skyline and distorts your reflection in the most wonderfully warped ways. It's endlessly fun to walk around, under, and through for a new perspective every time. The Crown Fountain is another truly unique art piece that features two 50-foot glass block towers that project ever-changing faces of Chicagoans. Watch as water spouts from their mouths (especially delightful on a warm day!), creating a playful splash pad that's a hit with kids and adults alike.
Pro-tip for those perfect, crowd-free photos: Set your alarm! Arrive early in the morning, right as the sun is coming up. You'll have these magnificent masterpieces almost entirely to yourself, allowing for serene, unobstructed shots of "The Bean" and the whimsical "Crown Fountain" before the crowds descend. For the motivated photographers, you can stop here first before you head to The Loop for brunch.
Wicker Park & Bucktown is one of those effortlessly cool neighborhoods that’s perfect for digging into Chicago’s local culture. Get ready for some seriously fun vintage thrifting, where you can unearth everything from retro band tees and classic denim to one-of-a-kind dresses and quirky accessories. The neighborhood is also a vinyl lover's paradise with established giants like Reckless Records (a Chicago institution!) to smaller, curated spots offering everything from rare jazz pressings to indie rock and punk.
A visit to Original Mindy's Hot Chocolate is an absolute must before you leave Chicago! While it's now Mindy's Bakery with a focus on pastries, you can still find those incredible, rich hot chocolates that put James Beard award-winning chef Mindy Segal on the map. Or if you lean toward ice cream over pastries, then Jeni's Splendid Ice Creams is the place to be. With unique, intensely flavored scoops like Brambleberry Crisp, Salty Caramel, or Gooey Butter Cake, Jeni's offers a truly "splendid" experience. And if you’re visiting during baseball season and are a sports fan, you absolutely have to tour Wrigley Field. Go behind the scenes, check out the dugouts, press box, and even step onto the hallowed field (on non-game days). Or, for a shot of pure basketball greatness, make your way to the United Center atrium and pose with "The Spirit," the legendary Michael Jordan statue that’s a tribute to one of the greatest athletes of all time.
From dazzling river cruises and heart-pounding tilts at 360 CHICAGO to indulging in iconic deep-dish pizza and discovering unique treasures in Wicker Park, this will be one spectacular weekend in Chicago. You’ll see the city from the sparkling lakefront to its towering rooftops, and even up close with masterpieces of art and architecture. Chicago truly delivers on every front: culture, cuisine, thrills, and charm. Now comes the fun part, coming to town and experiencing this itinerary for yourself!
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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 exhibit by local artist Coleman Smoll, making it an exciting spot for art lovers and Chicago visitors.
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, Guiding Light, created by expressive Chicago artist Coleman Smoll. This mural spans seven windows and includes hand-painted windows and floor, turning the observation deck into an immersive art experience.
Coleman Smoll’s Guiding Light transforms CloudWalk into a breathtaking tribute to Chicago’s skyline and neighborhoods. Through seven hand-painted window panels and a sprawling floor mural, Coleman blends bold colors, intricate details, and a sense of movement that captures the city’s energy. Each piece highlights a unique perspective of Chicago — from its iconic architecture to the vibrant communities that define its character — creating an immersive experience 1,000 feet above the city.
Coleman Smoll is a Chicago-based artist whose creative work spans oil painting, woodworking, drawing, tattooing, and graphic design. His art often explores themes of connection, transience, and reality — reflecting on consciousness, mortality, and the shared beauty of everyday life.
For Guiding Light, Coleman set out to capture the subtle threads that connect people across a city as vast as Chicago. His intricate mural features views of the John Hancock Center, a constant beacon in the skyline, as seen from neighborhoods throughout the city. Acting like a North Star for Chicagoans, the Hancock Tower becomes a unifying element, guiding viewers through a visual journey of vibrant color, detail, and perspective.
CloudWalk offers an unparalleled view of the city’s skyline, allowing visitors to see Chicago from a new angle. From its high vantage point, CloudWalk's open-air terrace delivers breathtaking views and a peaceful, elevated experience. Imagine soaking in the cityscape while surrounded by a masterpiece of modern art.
Guiding Light 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.
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 Coleman's exhibit 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.
This annual summer event brings thrilling aerial stunts and military flyovers to Chicago’s lakefront, with the U.S. Air Force Thunderbirds headlining this year’s show August 16-17th. From beaches to rooftops, there are plenty of great spots around the city to catch the action. Here are 10 of our favorite viewing locations.
Address: 875 N Michigan Ave, 94th Floor, Chicago, IL 60611
Catch the jets soaring past our windows from 1,000 feet above the city. Perched on the 94th floor of the former John Hancock Center, 360 CHICAGO gives you front-row views of Lake Michigan, the skyline, and the Air & Water Show like nowhere else. Don’t forget to stop by CloudBar for a limited-time Air & Water Show cocktail crafted just for the occasion.
To complete the experience, we’ll be broadcasting WBBM Newsradio throughout the observation deck so you can hear live commentary as the action unfolds!
Address: 1600 N Lake Shore Dr, Chicago, IL 60613
North Avenue Beach is the heart of the Air & Water Show where you’ll be right under all the action. With clear views of the lakefront and sky, this beach is a go-to where crowds gather early to claim their spot for the show. If you’re looking for a high-energy Chicago viewing experience, this is it!
Address: 1000 N Lake Shore Dr, Chicago, IL 60611
This is another great vantage point to watch the show, especially for those coming from the city. Oak Street Beach is easily accessible and offers sand, Lake Michigan swimming and two great beach bars to enjoy while you watch.
Address: 2401 N Lake Shore Dr, Chicago, IL 60614
Located along the shoreline, this historic venue offers lakefront views and a relaxed atmosphere that’s perfect for watching the jets fly by. With a restaurant and bar on site, grab a drink, kick back and enjoy the show at Theater on the Lake.
Address: 1000 E Grand Ave, Chicago, IL 60611
As the largest rooftop bar in the country, Offshore Rooftop offers incredible panoramic views of Lake Michigan. Catch the show with a cocktail in hand and snap photos of the planes soaring over the water and across the skyline.
Address: E Ohio St & N Lake Shore Dr, Chicago, IL 60611
Tucked away near Ohio Street Beach, this hidden gem is a peaceful spot to watch the show. With skyline views to the south and open skies to the east, Olive Park is a favorite among photographers and locals.
Address: 1603 N Lake Shore Dr, Chicago, IL 60611
This lakefront venue is hosting a lively viewing party with access to the patio and restaurant, plus the option to reserve VIP cabanas. Shore Club Chicago is one of the best ways to watch the show in style!
Address: 1603 N Lake Shore Dr, Chicago, IL 60611 (Located on North Avenue Beach)
Castaways is an iconic blue-and-white boat-shaped beach house that is the place to party during the Air & Water Show. Expect open bar packages, loud music and direct views of the jets soaring above the city.
Address: 1816 N Clark St, Chicago, IL 60614
Atop Hotel Lincoln, just steps from Lincoln Park, The J. Parker rooftop gives you a chic and elevated view of the action. With small plates, cocktails and lake views, it’s a laid-back yet stylish place to catch the show.
Address: Boarding Locations Vary
Take your Air & Water Show experience to the water with a City Cruise tour! Enjoy food, drinks and music as you take in views of the jets soaring high above the city skyline from Lake Michigan.
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Planning a trip to Chicago and dreading the inevitable eye-rolls and "I'm bored" whispers from your teens? The Windy City might just surprise you (and them!). We've put together the ultimate guide to making Chicago actually fun for your teen, packed with experiences that are definitely not lame. Get ready to swap their normal sighs for smiles, because we're talking epic views, interactive art, brain-bending museums, and, most importantly, food they'll actually want to eat.
After viewing downtown from the water, it’s time to head up, way up, for a bird’s eye view. 360 Chicago is a fantastic spot for teenagers looking for more than just a pretty panorama. Sure, the 94th-floor observation deck offers jaw-dropping 360-degree views of the Chicago skyline, Lake Michigan, and even four surrounding states on a clear day. But often the biggest attraction for teens is TILT! Imagine leaning out, face-first, over Michigan Avenue from 1,000 feet up! This enclosed, glass and steel platform slowly tilts outward, giving you a unique perspective of the city below. It's a safe but exhilarating experience that's a total blast.
Then stroll around the outdoor art exhibit featuring local artists. Plus, you can grab some cool drinks and snacks at CloudBar, including the teen-favorite mocktails Rainbow Beach and Midway, or other non-alcoholic beverages. Kick back together and toast the cityscape stretching out before you. And if you time your visit just right, you can do all this while catching a front-row seat to an awe-inspiring sunset.
Most everyone loves riding on a boat, even famously unagreeable teenagers. Add in extra points for insta-worthy views of Chicago’s famous landmarks that your teen can share with their friends back home. Along the way, expert guides will share the fascinating stories behind Chicago’s iconic architecture that appeal more to the parents.
Glide along the Chicago River, past masterpieces like the soaring Willis Tower, the unique corncob-shaped Marina City, the elegant Wrigley Building, and so many more, while learning how Chicago became a global architectural innovator. Whether you're an architecture buff or just looking for a super cool way to see the city with your kids, these 75-90 minute tours offer stunning panoramic views, comfortable seating (both open-air and climate-controlled), and often a cash bar for refreshments. If this isn’t thrilling enough for your family, you can up the adrenaline level with a speedboat tour on the Chicago River and Lake Michigan.
A lot of teens groan at the mention of touring an art museum, but The Art Institute of Chicago is actually packed with awesome stuff for teens. It's not just about staring at old paintings (though they have those too, and some are pretty cool!). Your family can kick things off by downloading their Teen Audio Guide on the official mobile app, where you'll hear other Chicago teens talk about the art. You can even use their "My Museum Tour" builder to create a personalized tour of your favorite pieces, maybe focusing on topics that interest your teen such as fashion, Black artists, or even mythical creatures.
Then head over to the ever-changing outdoor art gallery at the Wabash Arts Corridor in Chicago's South Loop. This place is a "living urban canvas" where ordinary building walls and alleys have been transformed into a massive showcase of incredible street art, murals, and installations. For teens, it's like a giant scavenger hunt for awesome photo ops and thought-provoking pieces. You can wander around discovering massive, colorful murals by local and international artists, often with cool messages or unique styles.
Columbia College Chicago students even get involved in creating new pieces, so there's always something fresh to see. It's totally free, super walkable, and gives you a chance to experience art in a totally different, dynamic way. There’s also dozens of restaurants nearby, so after exploring the art, you can walk over to a nearby restaurant and savor some delicious local cuisine.
At the Museum of Illusions, get ready for your brain to do some gymnastics. This place is all about visual tricks, optical illusions, and interactive exhibits that will have you questioning everything you view. Seemingly defy gravity in the Anti-Gravity Room or get lost in the dizzying Vortex Tunnel. Every exhibit comes with an explanation of the science behind the illusion, making it a cool blend of education and pure amazement.
Then at the Griffin Museum of Science and Industry, you can explore hands-on exhibits on everything from outer space to the depths of a coal mine. Teens will love stepping inside a real German U-505 submarine, experiencing simulated tornadoes and tsunamis in Science Storms, and exploring the incredible Great Train Story model railroad. You can even check out a real United 727 airplane!
At the Color Factory, prepare to be immersed in a world of pure imagination and, well, color. This interactive art experience is packed with unique rooms and installations that are designed to engage all your senses. Walk through vibrant ball pits, dance under confetti showers, snack on colorful treats, and discover whimsical spaces that are perfect for snapping epic, shareable photos.
And then there's the Sloomoo Institute, a dream come true for anyone who loves slime. Make your own custom slime at the DIY bar, explore different textures and scents, plunge your hands into giant slime vats, and even walk on a slime lake. For those who really want to be “immersed” in the slime experience, there’s Sloomoo Falls where you get to stand beneath, you guessed it, a slime waterfall.
No visit is complete without trying the famous Chicago-style deep dish pizza. Lou Malnati’s and Giordano’s are considered two of the best places to grab a slice (or two or three). What, exactly, is Chicago-style deep dish pizza? As the name suggests, it’s baked in a deep dish, with a thick buttery, flaky crust with a layered construction, often with cheese on the bottom and a thick layer of chunky tomato sauce on top—so come hungry!
Portillo’s hot dogs are another staple on the local food scene, and with numerous locations, you’re never far from their famous Chicago-style hot dog, which is a crowd pleaser for teens and parents alike. And if you’re wondering what a Chicago-style hot dog is, it has that classic “snap” in every bite. This comes from its many ingredients: sport peppers, kosher pickle, sliced tomatoes, chopped onions, celery salt, relish, mustard that are all piled on a juicy hot dog in a poppy seed bun.
And the best for last—vacation is the time to indulge in some delicious desserts. JoJo’s shakeBAR is one of the sweetest spots in town. There’s milkshakes, and then there’s JoJo milkshakes that look like sugary works of art almost too mesmerizing to eat. Snapping some pics with your shake is a must before digging in. They also serve hearty lunch and dinner dishes to balance out the sugar rush. Jeni’s Ice Cream is also a favorite summertime treat, with multiple locations offering scoops of delectable flavors like brambleberry crisp, sweet cream biscuits & peach jam, darkest chocolate, and the list goes on.
Chicago truly has something to spark even the most discerning teen's interest, from leaning into exhilaration at 360 CHICAGO and a speedboat architecture tour to immersive museums and delicious eats. Ditch the anxiety/exhaustion that can often accompany traveling with teens, embrace the adventure, and get ready to make some unforgettable family memories in Chicago. Your teenagers might even… dare we say it… thank you!
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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.
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 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.
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.
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.
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.
If you have time during your visit to the Windy City, check out one of these special-interest locations.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
Lake Michigan is home to all kinds of fun activities and interesting sights for first-time tourists and locals alike.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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 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 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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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!
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.
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.
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.
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.
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.
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!
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!
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.
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.
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.
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!
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.
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.
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!
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
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.
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.
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.
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.
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.
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.
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.
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!
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!
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!
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/
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!
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.
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. 
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/
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.
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. 
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.
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. 
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!
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. 
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.
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.
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. 
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
Photo credit: theaviary.com
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.
Photo credit: emptybottle.com
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.
Photo credit: the-dawson.com
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.
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.
Photo credit: musicboxtheatre.com
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.
Photocredit: https://revbrew.com/
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.
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.
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.
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.
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.
Photo credit: bobbysbikehike.com
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.
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. 
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?
Photo credit: ghostcitytours.com
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. 
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.
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.
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.
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.
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.
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.
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.
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.
Many Chicago museums offer free admission on certain days during the winter, so be sure to plan your visits accordingly.
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.
Stay warm and connect with nature year-round at one of Chicago’s indoor gardens.
The Lincoln Park Conservatory is housed in a beautiful Victorian greenhouse built in the 1800s. Entry is free, with reservations highly recommended.
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!
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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