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!
If you're looking for truly unforgettable date night ideas in Chicago, plan a special outing more than 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 out 30-degrees 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.
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.
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/
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.
One of Chicago’s most famous institutions, The Second City is no ordinary comedy club; it’s the improv comedy home of some of the brightest stars in entertainment, including Tina Fey, Steve Carrell, Martin Short and dozens more. 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!
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. A Chicago favorite for almost 50 years, 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.
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!
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.
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. 
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. 
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.
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.
One of the last remaining free-admission zoos in the country. 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. 
For one of the most romantic anniversary date ideas in Chicago, book a session at AIRE Ancient Baths in River West. This restored factory dates back to 1902 and 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/
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.
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.
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.
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!
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/
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. 
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
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
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.
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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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.
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.
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.
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.
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.
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.
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.
Last updated: September 22, 2025
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!
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.
If you've got just one day to spend in Chicago, head downtown and visit one of the city's iconic landmarks.
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.
If it's more of an indoors kind of day in Chicago, visit 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.
If you want to see the whole city in a day -- literally -- you'll have to get above it all. See Chicago from 94 stories at 360 Chicago for the perfect midday highlight.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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 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.
875 N. Michigan Avenue 94th Floor
Daily 9 am - 11 pm. The last entry is at 10 pm.
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.
North Michigan Avenue
Daily 9 am - 10 pm
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!
1200 S DuSable Lake Shore Drive
Daily 9 am - 6 pm
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.
Washington (George) Park, 740 East 56th Place
Wed-Sun, 11:00 am - 4:00 pm
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.
Check the admission page to see if you qualify for free admission.
1805 N. Ridgeway Avenue
Daily 6 am - 11 pm
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.
337 E. Randolph Street
Starting at 6 am - 9 pm. Times vary according to the activity.
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.
111 E. Wacker Drive, Suite 1321
Sun - Thu, 9 am - 5 pm
Fri & Sat, 9 am - 7 pm
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.
22 E Wacker Drive
Daily 6 am - 11 pm
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.
Things to do on or along the Riverwalk:
1614 E. 113th Street
Thu-Sun, 11 am - 3 pm
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.
5700 S. DuSable Lake Shore Drive
Daily, 9:30 am - 5:30 pm
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.
See exciting new exhibits always on display
1300 S DuSable Lake Shore Drive
Daily 9 am - 4 pm
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.
78 E. Washington Street
Daily 10 am - 5 pm
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.
1616 N Wells Street, 2nd Floor
Mon-Thu, 10 am - 11 pm
Fri-Sun, 10 am - 12 am
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.
1852 W. 19th Street
Tue-Sun, 10 am - 5 pm
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.
Cermak Road and Wentworth Avenue
24 hours
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.
1060 W. Addison Street
See the game and tour schedule.
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.
The Loop Community Area
Daily, 6 am - 11 pm
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.
1601 N. Clark Street
Tues–Sat, 9:30 am - 4:30 pm
Sun, 12:00 pm - 5:00 pm
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.
111 S Michigan Avenue
Thu-Mon, 11 am - 8 pm
Tue-Wed, Closed
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.
From Ardmore Ave. on the north to 71st St. on the south, Chicago
Open Daily
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.
4802 N Broadway Avenue
Daily 4 pm - 1 am
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.
1400 S Lakeshore Drive
Daily 9 am - 5 pm
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.
600 E. Grand Avenue
Sun-Thu, 11 am - 9 pm
Fri-Sat, 11 am - 10 pm
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.
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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Location: 201 E Randolph Street
Proposal Photography Permit: Required
Permit Fee: $35 application fee +$45 photography fee/hour
In the heart of downtown Chicago lies Millennium Park, a favorite spot for a proposal amidst iconic city landmarks. The park's famed Cloud Gate sculpture, affectionately known as "The Bean," provides a reflective, mesmerizing backdrop perfect for the occasion. Beyond The Bean, the park's beautifully landscaped gardens and impressive cityscape views offer various romantic spots for getting down on one knee. Even more, you can heighten the ambiance by timing your proposal with one of the park's regular concerts or public events. While Millennium Park operates from 6 am to 11 pm, you'll want to keep in mind that peak hours and events may increase the number of spectators to your special moment.
Location: 201 E. Randolph St., between Monroe St. and Columbus Ave
Proposal Photography Permit: Required
Permit Fee: $35 application fee +$45 photography fee/hour
Pop the question at Lurie Garden, a magnificent five-acre sanctuary famed for its sustainable design and gorgeous perennial garden located at Millenium Park. This spot would offer a peaceful and visually striking setting for your marriage proposal. The contrasting scenery of native plants against the city's towering skyline provides a gorgeous backdrop, blending nature's beauty with architectural grandeur. Planning your proposal during the blooming season, from late spring through early fall, will showcase the garden at its most vibrant, making it a great choice for your special moment. In one word? Beautiful.
Location: 500 N Lake Shore Dr, Chicago
Proposal Photography Permit: Not Required
Permit Fee: None
Step into Milton Lee Olive Park, a hidden gem away from the hustle and bustle, waiting to be the stage for your grand proposal moment! This isn’t just any spot; it’s where Lake Michigan meets the vibrant Chicago skyline, creating a magnificent canvas that's both wildly natural and unmistakably urban. For couples who chase extraordinary experiences, this park is the perfect spot for you to declare your love. Imagine—the privacy, the secluded paths, all leading to that one magical moment where you pop the question against a backdrop nothing short of spectacular. No permits, no fuss, just ensure you make your move before the clock strikes 11 pm. Here’s your chance to step up, embrace the moment, and mark the beginning of your forever.
Location: 875 N Michigan Avenue
Proposal Photography Permit: Not Required
Permit fee: None
See Proposal Package
Transform your proposal into a landmark moment at 360 CHICAGO! Perched on the 94th floor of the former John Hancock Building, this observation deck gifts you a breathtaking 360-degree panorama that sprawls over Chicago and spills into the majestic Lake Michigan. Envision taking your love to new heights, proposing amidst a canvas of sunset or the city's luminous night lights. The Chicago Proposal Package is designed to fuel that romance with all the right touches. It offers you a private space with unmatched views, captivating "Marry Me" lights, a trail of rose petals, adrenaline-pumping TILT thrill ride tickets for two, and a duo of drinks from CloudBar's Sip Menu. Once there, you're invited to immerse yourselves entirely and stay as long as you like. Seize this opportunity to etch your moment in eternity, showcasing the unstoppable force of your love. Let 360 CHICAGO be the launchpad for your journey together. Propel your love story into the stratosphere, where it rightfully belongs!
Location: 2001 N Clark St, Chicago
Proposal Photography Permit: Yes
Permit Fee: $150 /hr photo session
Lincoln Park Zoo offers a whimsically romantic setting for those looking to pop the question amidst gardens, animals, architecture, and Chicago's skyline view. The enchanting backdrop of exotic animals and beautifully landscaped grounds provides a unique and lively atmosphere for a proposal. Whether you choose to kneel beside the tranquil swan pond, under the leafy embrace of the conservatory, or in front of your partner’s favorite animal exhibit, this location ensures an unforgettable moment. The zoo offers a playful setting that speaks to the adventurous spirit of love.
Location: Southern end of the zoo, east of Café Brauer 2121 N Stockton Drive
Proposal Photography Permit: Yes
Permit Fee: $150 /hr photo session
Lincoln Park is a haven for nature lovers and a picturesque choice for a proposal. This expansive park is adorned with sprawling gardens, tranquil ponds, and scenic pathways, offering a variety of enchanting settings. Opt for a bridge overlooking the South Pond for a beautiful view that encapsulates the essence of nature in the city. Beyond its natural charm, this idyllic park is known for its peaceful ambiance that invites lovers to express their heartfelt feelings. Plus, with its proximity to neighboring eateries and fantastic cityscape views, your proposal can easily be extended into a romantic date, marking an unforgettable chapter in your love story.
Location: 125 W Fullerton Parkway Suite 4800
Proposal Permit: Required
Permit Fee: $150.00
Immerse yourself in nature's serenity at The Alfred Caldwell Lily Pool within Lincoln Park. This tranquil oasis is characterized by its meandering stone pathways, native plants, and, most notably, the picturesque lily pool that provides a serene and intimate location to pop the question. The Lily Pool is open to visitors from mid-April through early November, from sunrise to sunset.
Location: Southernmost end of the zoo, east of Café Brauer and Farm-in-the-Zoo 2121 N Stockton Drive
Proposal Photography Permit: Required
Permit Fee: $125.00
This architectural beauty in Lincoln Park creates a gorgeous setting for an engagement. The Honeycomb Structure, officially known as the People's Gas Pavilion, is a marvel of modern design, featuring a lattice-like steel network forming an expansive canopy above a lush green landscape. The interplay of light and shadow through its geometric patterns provides a visually stunning setting. Picture the moment you ask your person to marry you, enveloped by this architectural masterpiece, with nature as your witness. This spot not only offers a unique backdrop for such a pivotal moment, and also symbolizes the interconnectedness of your future together.
Location: 5700 S Lake Shore Drive
Proposal Photography Permit: Inquire
Permit Fee: Inquire
Ignite a spark of discovery and innovation at the Museum of Science and Industry for your proposal. This place is especially appealing to couples who share a passion for science, exploration, and learning. This iconic venue, one of the largest science museums in the world, offers an extraordinary array of exhibits that provide a dynamic and interactive backdrop for popping the question. Imagine the excitement of proposing amidst groundbreaking scientific achievements, from standing under a massive suspended aircraft to the shadows of a towering dinosaur skeleton! It will be a moment that your loved one least expects. Check with Museum staff for any required permissions or fees related to events or photography. Operating hours vary, so make sure to plan your surprise around a time when your favorite exhibits are accessible.
Location: 1601 N. Lake Shore Drive
Proposal Photography Permit: Not Required
Permit Fee: None
It's one of the city's most popular beaches, with some of the best views of the city and Lake Michigan, hands down! Imagine walking hand in hand along the sandy shores of North Avenue Beach, pausing as the sky is painted in orange and purple hues. At this moment, as the bustling city seems to stand still, presenting your beloved with the ultimate question here makes for an exceptionally picturesque and heartfelt moment. Not only is this location easily accessible, but it also does not require a permit for proposals, making it a cost-effective yet heartwarming choice. Keep in mind, though, that this public space is most peaceful during early mornings or late evenings.
Location: South bank of the Chicago River
Proposal Photography Permit: Not Required
Permit Fee: None
Take a stroll along the Chicago Riverwalk for an enchanting proposal experience. This waterside promenade weaves through the heart of the city with its captivating views. Lined with impressive skyscrapers and bridged by historic walkways, the Riverwalk provides a unique blend of natural beauty and architectural marvels. Choose a spot near one of the many iconic landmarks to pop the question, which will likely be very unexpected! The ideal time for a more serene moment would be in the early morning or late evening, avoiding significant crowd times, typically in the mid-afternoon and on weekends.
Location: 1200 W Randolph Street
Proposal Permit: None
Permit Fee: None; inquire about private space/dining and drink experience
Do you and your partner love fine wines and an intimate setting? Look no further than the City Winery Chicago, which offers a lovely proposal location. Located on the vibrant Chicago Riverwalk, this venue combines urban sophistication with the charm of wine country, making it an idyllic spot for this special moment. With its customizable event spaces, you can curate an ambiance that reflects your love story, whether it's a private barrel room illuminated by candlelight or a scenic outdoor patio with river views. Although the City Winery does not require permits for small, informal gatherings, securing a private space for your proposal might involve a reservation fee and should be arranged directly with the venue. This ensures your moment is as seamless as it is memorable. Whether over a glass of their finest vintage or a custom dining experience, proposing at City Winery promises romance and tasty libations.
Location: Center of Grant Park, 301 S Columbus Drive
Proposal Permit: Required
Permit Fee: $35 application fee + $45 photography fee
This historic fountain (Remember the opening scene of Married With Children?) is one of the largest in the world and provides a visually stunning background for your special moment with your love because of its rococo-style design and dazzling water displays. The fountain's water shows and Chicago's skyline in the background create a romantic atmosphere, especially during the evening light and music performances from April to October. For an added wow factor, plan for the proposal to happen when the fountain's water display is in full swing. The park is open from 6 am to 11 pm, offering flexibility for your proposal plans. However, be mindful of public events that might coincide with your planned date. Visiting the Buckingham Fountain will deliver a visually spectacular moment.
Location: 1000 Lake Cook Rd, Glencoe, IL (20 miles from Chicago)
Proposal Photography Permit: Required
Available daily 10 a.m., 12 p.m., and 2 p.m.
Permit Fee: $250 Includes parking for two passenger vehicles
Escape to a world where nature's beauty unfolds at every turn at the Chicago Botanic Garden. This sprawling sanctuary offers an idyllic setting for your proposal if your partner loves meticulously curated gardens and tranquil water features. Its vast array of landscapes, from the romantic English Walled Garden to the serene Japanese Garden, provides a variety of locations perfect for dropping to one knee. Choosing this location for your special moment ensures a backdrop filled with natural beauty and a tranquil atmosphere.
Location: 600 E Grand Ave
Proposal Photography Permit: Not required
Permit Fee: Not required
Looking for an engagement location that will deliver fun and energy? Navy Pier, stretching into Lake Michigan, offers a captivating backdrop for your proposal. This iconic Chicago landmark is home to the Centennial Wheel, providing a unique opportunity to pop the question high above the city with panoramic views of the skyline and lake. The pier's lively atmosphere, filled with gardens, restaurants, and attractions, adds a festive touch to your special moment. You won't have a private location, but you will have a blast for your big day.
Location: 23rd Floor, London House Chicago. 85 E Wacker Drive
Proposal Permit: Required
Permit Fee: Inquire
Perched atop the luxurious London House Chicago, The Cupola (a private outdoor section on the roof of London House) offers an intimate and breathtaking venue for a marriage proposal. This exclusive space boasts Chicago skyline views of the Chicago River, creating a dramatic and unforgettable scene. The Cupola's elegance and privacy make it ideal for a special moment away from the city below. The team at London House can top off your evening with a special dinner menu to celebrate your special occasion.
This is one of the classic summer activities in Chicago. Every Wednesday at 9 pm and Saturday at 10 pm, starting Memorial Day weekend through to Labor Day weekend, marvel at the dazzling fireworks spectacle put on all summer long at Chicago’s famous Navy Pier. Take in the show from any of the beaches along the lake, from the pier itself, or book a romantic dinner cruise to see them from the water in style.
For the most stunning vantage point (like in this photo),head to the 360 CHICAGO Observation Deck to catch the fireworks from 94 floors up!
The boys of summer are in full swing as the Cubbies take to the diamond this summer in front of their loyal fans at Wrigley Field. Even if you’re not into baseball, Wrigley Field is designated as a historic landmark, and is one of the two oldest operating Major League parks in the country. Can you guess the other one?
Get your Cubs tickets now!
Situated in the lush Logan Square neighborhood, the 606 Trail is Chicago’s answer to the High Line, and summer in Chicago is the perfect backdrop. At almost three miles long, the beautiful elevated park used to be a railroad track for the city’s famous “L” Train. Walk, skate, or ride your bike and discover art installations, murals, and other community engagement projects. The 606 is also a great place to bring a picnic!
The incredible story of Chicago might best be told through its captivating architecture. These guided cruises are the perfect way to relax, take in the sights, and learn some of the amazing history behind the city’s most iconic buildings.
Reserve your Architecture Cruise in advance, these are popular tours!
Chicago has miles of lakefront beaches and spots like this to enjoy the gorgeous skyline from literally every angle. Plan a drink on a boat, head to the beach such as Foster Beach, North Avenue Beach, or Rainbow Beach, or find somewhere to dine al fresco with views from above. You've got options in Chicago!
If big adventure is what you’re after, head just 22 miles outside of Chicago to The Forge: Lemont Quarries, where you’ll find outdoor activities for the whole family. No matter your age or fitness level, there’s something for everyone at The Forge, including climbing, ziplining, competitive activities like laser tag, hiking, kayaking, and so much more. There are even several dining options to refuel after your adventure.
Check out all the fun at The Forge, and book your adventure now!
The Forge also features a full summer schedule of concerts, live music, and events too.
Take in breathtaking panoramic views of the whole city from 1,030 feet above the famed Magnificent Mile at the 360 CHICAGO Observation Deck at the top of the former John Hancock Center. Visit CloudBar for a Sip and View, and if excitement is what you’re after, step into TILT, the world’s highest thrill ride. It's no surprise why its one of the top things to do in Chicago in summer.
Get your tickets now for 360 CHICAGO and skip the line!
From June 26, 2025, to August 7, 2025 (every Monday and Thursday) at Millennium Park’s Jay Pritzker Pavilion, enjoy music from around the world and right here in Chi-town, featuring artists both emerging and established. This summer’s series always kicks off with a renowned music artist, so check back to see who is headlining the series this year.
Admission to concerts is always free, and the park is open from 6:30 p.m. to 11 p.m. View the summer events schedule for super helpful information about planning your visit
Spend your summer exploring the City of Chicago's wide array of farmer's markets! Stocking up on freshly grown produce, aromatic flowers, pre-prepared meals, handmade goods, and uncommon trinkets is just a short journey away. From May to October, you can visit the longest-running market in Chicago - the iconic Daley Plaza Farmers Market - as well as the storied Maxwell Street Market and numerous community markets. For a full list of markets, check out the map and date schedule for more information.
Summer in Chicago isn't complete without a good festival. Grant Park is home to the only free outdoor classical music festival in the country. Featuring the Grant Park Symphony Orchestra and Chorus, along with a bevy of guest musicians and conductors, performances take place throughout the summer, and the lineup of performances this year look fantastic. The music festival starts in June toAugust.
Since 1980, Chicago's food scene has come alive during summertime with a fantastic range of restaurants and eateries showcasing the city's incredible culinary art and diversity. The festival gets going in Marquette Park on June 28th, 2025, then to Pullman Park on July 19th, 2025, then Albany Park on August 9th, 2025. The final weekend returns to Grant Park on September 5th - 7th, 2025. Don't forget, entry is free! For more details, please visit the Taste of Chicago.
Mark your calendars for Sunday, June 29th, 2025 for the most joyous, colorful, fun events of the year. The Chicago Pride Parade is one of the biggest Pride festivals in the world. This year’s theme, United in Pride, showcases the power of diversity, unity, and the power of love as an unstoppable force for good. For more details, please visit the Chicago Price Parade.
The City of Chicago is delighted to present the Air and Water Show on August 16th & 17th, 2025, with a rehearsal on Friday August 15th. Now in its 63rd year, with a reported attendance of up to two million annually, you’ll see performances from a selection of top civilian and military pilots and aircraft, such as the U.S. Navy Blue Angels, the U.S. Air Force Thunderbirds, and the U.S. Army Parachute Team Golden Knights. There’s no public seating areas available at the event, so you’re encouraged to stake out their viewing spots early along the lakefront from Fullerton to Oak Street, with North Avenue Beach as the focal point.
To make the most of the show, consider taking in the views from 360 CHICAGO, with its prime and uninterrupted panoramic views of the show.
The world-renowned Lollapalooza music festival returns to its permanent home in Chicago on July 31st to August 3rd, 2025, taking over Grant Park with 9 stages and over 170 bands. Fans can look forward to spectacular performances from Tyler, The Creator, Luke Combs, Olivia Rodrigo, Kron, Rüfüs Del Sol, Sabrina Carpenter, A$AP Rocky, and so many more.
Available ticketing options include General Admission, VIP, and Platinum, as well as one-day, two-day, and four-day passes. For the complete lineup and ticket information, check out Lollapalooza's official website. Get your hands on the Lolla lineup, details, and tickets now!
There’s so much to do this time of year in the windy city! We hope this Chicago Summer Guide is helpful as you and your loved ones get out into the warm weather and take in all the city has to offer. While you're here, explore the vibrant Chicago Neighborhoods using this handy guide for fun things to do, cultural flavors, and great views of the city.
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Enjoy the highest bar in Chicago and the most exceptional views of the city skyline, hands down! Located at the 360 CHICAGO Observation Deck on the 94th floor of the former John Hancock Building, you’ll get unparalleled 360-degree views of the Chicago skyline and Lake Michigan. Get the best seat in the house at CloudBar, a modern, sleek lounge where European design meets Chicago flare. Peruse the snack list, or order a unique cocktail (or mocktail) from the menu. Try a Wild and Personable, a Gold Coast Manhattan, or other drinks inspired by the culture and energy of the Chicago neighborhoods.
CloudBar, the top bar in Chicago with a view, is open from 9 am-11 pm daily. Special tickets are available for admission on the Observation Deck, which include a drink from a select menu (Sip & View Ticket) or a Sip, TILT, and View Ticket, which includes a ride on TILT— one of the highest thrill rides in the world. Enter with an admission ticket and stay as long as you like!
Neighborhood: Streeterville
Hours:
• Monday – Thursday: 4:00 PM – 12:00 AM
• Friday – Saturday: 2:00 PM – 1:00 AM
• Sunday: 2:00 PM – 12:00 AM
Distance from 360 CHICAGO: 5–7 minute walk.
Reservations: Limited reservations accepted for parties ≤8 via Tock (outdoor terrace also).
Elevator Pitch: A chic rooftop lounge above Michigan Ave delivering bold global cocktails in a refined setting.
Z Bar, in one word, is classy. It is a luxury, upscale rooftop bar concept located on the 6th floor of The Peninsula Chicago Hotel on Michigan Avenue. Z Bar combines the allure of global cuisine and drinks with a view along downtown's Magnificent Mile. World-renowned mixologists curate the bar's inventive cocktail menu that guarantees a great hangout whether you're enjoying the environment amid the chic, cosmopolitan interior or basking in the open air on the terrace.
Neighborhood: Streeterville / Navy Pier
Hours:
• Monday–Thursday: 11:00 AM – 11:00 PM
• Friday–Saturday: 11:00 AM – 12:00 AM
• Sunday: 11:00 AM – 10:00 PM
Distance from 360 CHICAGO: 10–12 minute rideshare or car.
Reservations: Recommended for parties of 8 or more; outdoor seating is first-come first-serve; last reservation is one hour before closing.
Elevator Pitch: A massive, panoramic rooftop on Navy Pier with sweeping skyline views and full bar.
Imagine 36,000 square feet of indoor and outdoor rooftop and bar space! You can find it at Offshore Rooftop & Bar, America's largest rooftop venue at Navy Pier. Visit this place during a trip to the iconic pier to sample from the list of inventive bar snacks, shared plates, wine, cocktails, and craft beers. The bar juts out into Lake Michigan and offers fantastic views of the Chicago skyline and the lake. The space is modern and sleek, and for chilly days, its fire pits and comfortable seating areas will make you want to linger here a little longer.
Neighborhood: The Loop / Downtown
Hours:
• Tue–Thu: 3:00 PM – 10:00 PM
• Fri–Sat: 3:00 PM – 11:00 PM
• (Closed Sunday/Monday)
Enjoy the culture and flavors of South America without ever leaving Chicago's financial district! Boleo lives on the 15th floor of the Kimpton Gray Hotel and is known for its rain-or-shine retractable glass roof. Inspired by South America's vibrant colors and textures, the bar's design creates a warm and inviting ambiance, perfect for lively evenings with friends or intimate nights out. The space is infused with the sounds of live Latin music that complements the rich flavors of the Peruvian and Argentinean-inspired street food menu. Sip on a Pisco Sour or a Smoky Paloma crafted by expert mixologists. Whether you're here to enjoy the music or to savor the intricately designed cocktails, Boleo is an exciting destination among the rooftop bars in Chicago.
Neighborhood: The Loop / Downtown
Hours:
• Mon–Thu: 4:00 PM – 12:00 AM
• Fri–Sat: 2:00 PM – 12:00 AM
• Sunday: Closed
Reservations: Bar/rooftop primarily first-come/first-served.
Elevator Pitch: A modern indoor/outdoor rooftop bar three stories up, offering skyline views and a vibrant downtown bar atmosphere.
Discover Raised, located in the heart of the Loop. This inviting space blends the city's architectural grandeur in an industrial chic ambiance with garden-inspired decor, which gives this open-air venue an urban yet relaxed vibe after a busy day in the city. With views that stretch over the Chicago River and into the city's sprawling skyline, Raised offers a picturesque setting for enjoying its extensive food and drink menu. Here, local craft brews, imaginative cocktails, and a curated selection of American dishes take center stage. Raised is a popular destination for those looking to embrace Chicago's rooftop culture.
Neighborhood: The Loop / Downtown
Hours:
Reservations: Not required, but highly recommended.
Elevator Pitch: Chic rooftop lounge atop The Wit, blending city views with an elevated nightlife scene and stylish ambiance.
Roof on the Wit, a pioneering rooftop lounge, is perched on the 27th floor of the Wit Hotel, steps away from the iconic Chicago Theatre. Guests are welcomed into a space that combines the allure of an elegant cocktail party with the energy of a premier nightclub. The Roof on the Wit has a retractable roof that guarantees an unforgettable experience regardless of the weather. The menu is equally interesting, with an impressive array of drinks and a vast food menu of shareable plates, pizza, sushi, and more. This rooftop bar not only captivates with its panoramic views of the city's skyline but also its unique design, featuring fire pits and sleek, modern seating areas.
Downtown-The Loop
Neighborhood: The Loop / Downtown
Hours:
• Mon–Thu: 11:00 AM – 11:00 PM
• Fri: 11:00 AM – 12:00 AM
• Sat: 10:00 AM – 12:00 AM
• Sun: 10:00 AM – 11:00 PM
Distance from 360 CHICAGO: 5–7 minute walk.
Reservations: Encouraged via OpenTable; walk-ins accepted.
Elevator Pitch: Indoor/outdoor rooftop restaurant atop the Chicago Athletic Association with panoramic views of Millennium Park.
Neighborhood: The Loop / Downtown
Hours:
• Mon–Wed: 4:00 PM – 10:00 PM
• Thu: 4:00 PM – 12:00 AM
• Fri–Sat: 3:00 PM – 2:00 AM
• Sunday: 3:00 PM – 10:00 PM
Reservations: Table reservations / VIP / bottle service available.
Elevator Pitch: A rooftop lounge/clubbing experience 26 floors up, with DJs, craft cocktails, skyline views, and late-night vibes.
Cerise, a bar at the Virgin Hotels Chicago in the Loop neighborhood, offers a refreshing take on the rooftop bar experience with its energetic atmosphere and eclectic design. This 26th-floor bar commands an impressive view of downtown, serving as a perfect backdrop for evening escapades. Cerise is known for its bold cocktails, nightclub atmosphere, and a rotating roster of DJs that keep the atmosphere alive.
Neighborhood: The Loop / Downtown
Hours:
Mon – Thur: 9:00 PM – 11:00 PM
Fri – Sat: 9:00 AM – 12:00 AM
Sun: 9:00 AM – 11:00 PM
Reservations: Reservations accepted for seating.
Elevator Pitch: A refined rooftop terrace and lounge atop The Gwen hotel, offering seasonal cocktails, bites, and skyline views in an artful, designer setting.
Upstairs at the Gwen can be found on the 5th floor of the Gwen Hotel on the Magnificent Mile. This art deco-designed bar has sleek and contemporary lines and offers comfortable seating, cozy firepits, and large umbrellas and monitors to function in any season in the Windy City. The menu celebrates innovation and tradition in handcrafted cocktails like the Creole Maple Old Fashioned and the Mayan Mule. Upstairs at the Gwen is ideal for intimate gatherings and larger social outings.
Neighborhood: River North
Hours:
• Mon–Thu: 3:00 PM – 10:00 PM
• Fri–Sat: 3:00 PM – 11:00 PM
• Sunday: 3:00 PM – 10:00 PM
Reservations: Yes for smaller parties; walk-ins accepted when space permits.
Elevator Pitch: Open-air rooftop oasis atop the Hyatt Centric with panoramic skyline views, shareable bites, and craft cocktails.
Head to the 24th floor of the Hyatt Centric The Loop Chicago and find Aire Rooftop Bar, a refreshing retreat in the bustling River North neighborhood. This open-air bar boasts fantastic skyline views of the city and an exciting menu of Midwestern favorites, cocktails, and slushes for those hot summer days. Aire offers seasonal events and themed nights, transforming the space into an ever-evolving entertainment hub. Nestled amidst the architectural grandeur of Chicago, just moments away from Michigan Avenue, this rooftop bar is the place for a lively atmosphere.
Neighborhood: River North
Hours: 7:00 AM – 11:00 PM daily
Reservations: Available via OpenTable for dining/rooftop.
Elevator Pitch: Scenic 16th-floor terrace and bar at Trump International, offering sweeping river and city views in an elegant setting.
Terrace 16, located at the top of the Trump International Hotel & Tower boasts an enviable position overlooking the winding Chicago River and the city's skyline. This bar and restaurant celebrates American culinary flavors with dishes like the Terrace 16 Burger. You can explore a diverse selection of wines and inventive cocktails that perfectly complement the gastronomic offerings. With its contemporary aesthetics and sprawling indoor and outdoor space, Terrace 16 offers a refined ambiance perfect for any time in the day or evening. With a visit here, you'll feel like you're in the heartbeat of Chicago from this exciting vantage point.
Neighborhood: River North
Hours: 11:00 AM – 12:00 AM daily
Reservations: Available for seating. Walk-in access to rooftop when space available.
Elevator Pitch: Multi-level riverfront rooftop lounge with dramatic views of the Chicago River, elegant cocktails, and indoor/outdoor seating.
At the epicenter of Chicago's downtown, LH (LondonHouse) Rooftop sets the stage for an unmatched luxurious outing at the junction of Michigan Avenue and Wacker Drive. Get ready for a fantastic view of the Chicago River and the Magnificent Mile from its open-air rooftop on the 22nd floor. Service here is reserved for dining, so be sure to come hungry and make it a night of dinner and drinks with a view. Don’t forget to take advantage of the incredible Margarita menu. A visit to the LH Rooftop is an opportunity to bask in the grandeur of Chicago's outstanding architecture.
Neighborhood: River North
Hours:
• Wed–Fri: 7:00 PM – 4:00 AM
• Saturday: 7:00 PM – 5:00 AM
Reservations: Available for dinner and bottle service
Elevator Pitch: A multi-level lounge and rooftop garden offering late-night vibes, Deco-inspired design, and elevated social energy.
Celeste is a multi-level establishment built in 1888 that marries the charm of a classic cocktail lounge with the allure of a modern bar. This historic building allows guests to traverse different atmospheres, from the intimate ground floor Whiskey Lounge to the vibrant rooftop garden, each floor designed with Victorian-era decor and contemporary touches to give it a timeless elegance. This Chicago rooftop bar, known as The Garden, is a calming retreat amidst the urban landscape of Chicago, offering a serene spot to enjoy drinks (a.k.a. top-end bottle service) under the stars.
Neighborhood: River North
Hours:
• Mon–Fri: 4:00 PM – 2:00 AM
• Sat: 11:00 AM – 3:00 AM
• Sun: 11:00 AM – 12:00 AM
Reservations: Standard and VIP reservations available.
Elevator Pitch: Dynamic rooftop lounge and nightlife hub, combining dining, dancing, and skyline views in one venue.
Joy District stands as a beacon of nightlife and social gatherings. It's part sports bar, dance bar, and rooftop patio for people who want to party. The rooftop bar offers a lit-up nighttime space for gatherings with friends for cocktails, music, and nibbles on classic American small and large plates. Looking to elevate your night with a lot of energy and great skyline views in the distance? This is one of the Chicago rooftop bars to check out!
Neighborhood: River North
Hours:
• Mon–Thu: 2:00 PM – 12:00 AM
• Fri: 12:00 PM – 2:00 AM
• Sat: 11:00 AM – 2:00 AM
• Sun: 11:00 AM – 8:00 PM
Reservations: Recommended for smaller parties; party/groups booking available.
Elevator Pitch: Expansive indoor/outdoor “roofscape” atop The Godfrey, with retractable roof, fire pits, skyline views, and year-round energy.
Looking for an upscale lounge with a view? Head to the Godfrey Hotel's Rooftop for an elegant lounge with an indoor/outdoor space, including a sleek, retractable roof system, ensuring the party continues regardless of the weather. Sip as the city lights twinkle below on modern variations of lemonades, mojitos, and sangrias, and complement them with small plates like sushi rolls and shrimp tacos. The Godfrey hosts Kentucky Derby Parties, special events, or regular gatherings, day or night.
Neighborhood: Wicker Park
Hours:
• Sun–Thu: 5:00 PM – 12:00 AM
• Fri & Sat: 5:00 PM – 1:00 AM
Reservations: Walk-ins welcome; no reservation required for general seating.
Elevator Pitch: Sleek 13th-floor rooftop lounge at The Robey, blending indoor/outdoor ambiance with sweeping views and crafted cocktails.
The UP Room at The Robey Hotel provides an elevated drinking experience that mirrors the sophistication and style of Chicago itself. Situated on the 13th floor, the interior blends art déco elegance and contemporary comfort, providing a cozy yet stylish setting for intimate dates and casual gatherings. The velvet seating and warm lighting set against the backdrop of the Chicago skyline create an almost cinematic experience. Enjoy expertly crafted cocktails that blend classic Mixology with innovative twists. The UP Room at The Robey Hotel promises an unmatched atmosphere that captures the essence of rooftop bars in Chicago.
Neighborhood: Wicker Park
Hours:
• Mon–Thu: 4:00 PM – 10:00 PM
• Fri & Sat: 4:00 PM – 11:00 PM
• Sunday: 11:00 AM – 8:00 PM (brunch until 3:00 PM)
Reservations: Reservations or walk-ins accepted; table time limited (2 hours) and groups larger than 10 may not be accommodated.
Elevator Pitch: Trendy rooftop atop Hyatt Place Wicker Park, serving brunch, small bites, and craft cocktails with skyline views.
Wicker Park's Kennedy Rooftop, located at the top of the Hyatt Place Wicker Park, offers a fun and artsy atmosphere with great views of the Chicago Skyline. Head on the patio and play a giant game of Jenga with friends while sipping on a cocktail from its Oval Office and Presidential drink menu, or drop by for Happy Hour from 4-6 pm Monday through Friday. The Kennedy offers sharable plates and a sizeable Charcuterie Platter to satisfy the hunger and keep the fun going well into the night.
Neighborhood: Lincoln Park
Hours:
• Monday & Tuesday: 4:00 PM – 11:00 PM
• Wednesday & Thursday: 11:00 AM – 11:00 PM
• Friday: 11:00 AM – 12:00 AM
• Saturday: 10:00 AM – 12:00 AM
• Sunday: 10:00 AM – 10:00 PM
Reservations: Available via OpenTable for dining/rooftop.
Elevator Pitch: A rooftop lounge atop Hotel Lincoln with sweeping views of the lake and skyline, seasonal cocktails, and an airy atrium style setting.
Perched atop Hotel Lincoln in the beautiful Lincoln Park neighborhood is The J. Parker, one of the popular Chicago rooftop bars. This spot has some of the best views of Chicago that sweep across the city skyline and the vast expanse of Lake Michigan. This spot strikes a harmonious balance between elegance and affordability, with a diverse menu that caters to various tastes. J. Parker is known for its bottomless Mimosa and Bloody Mary's paired with its classic brunch. This spot is for you if you want food, drink, and views in a stylish yet laid-back setting.
Neighborhood: South Loop
Hours:
• Monday–Thursday: 4:00 PM – 11:00 PM
• Friday & Saturday: 4:00 PM – 1:00 AM
• Sunday: 4:00 PM – 11:00 PM
• Brunch hours (weekends): Saturday & Sunday from 11:00 AM – 3:00 PM
Reservations: Yes — via OpenTable for the restaurant/lounge portion; outdoor seating is often first-come, first-serve.
Elevator Pitch: A 22nd-floor, all-seasons rooftop concept with panoramic city & lake views, multiple bars, indoor lounge, terraces, fire pits, and a shares / chef-driven menu.
Elevating the dining and drinking scene in the South Loop, VU Rooftop Bar proudly stands 22 stories high, offering excellent views of Lake Michigan and the Chicago skyline. The bar's contemporary design, indoor lounge, and outdoor terrace make it the perfect spot to enjoy the city views and stay to indulge in a drink or dinner. The drink menu is overflowing with creative cocktails that can all be customized with or without spirits. For those with a sweet tooth, the Dessert Cocktail selections are sure to satisfy. Even on a chilly night, it's the spot to cozy up in front of the fire pit on the comfy couches and take in sparkling city lights.
Reservations: Available via OpenTable for dining/rooftop.
Elevator Pitch: A Mediterranean-inspired rooftop oasis in Fulton Market blending lush décor, firepits, and seasonal small plates & cocktails.
Transport yourself into a Mediterranean-meets California-inspired oasis on this 3rd-floor bar/restaurant, which offers an escape into a lush, botanical setting where olive trees and greenery frame the skyline views. Aba's menu is a celebration of Mediterranean flavors, with a focus on mezze, the shared plates that invite conversation and connection. The Smoky Garlic Hummus and Shawarma-Spiced Skirt Steak are just a taste of the culinary delights that await. Whether you're here for a delicious brunch or a serene evening, Aba's rooftop is a testament to the beauty of dining al fresco in Chicago.
Hours:
• Monday–Wednesday: 5:00 PM – 9:30 PM
• Thursday: 5:00 PM – 10:30 PM
• Friday & Saturday: 5:00 PM – 11:00 PM
• Sunday: 5:00 PM – 9:30 PM
Reservations: Yes — reservations required; walk-ins accepted when available.
Elevator Pitch: A sophisticated rooftop lounge 11 floors up, pairing Nobu-style small plates, signature cocktails, and sweeping skyline vistas.
Rooftop at Nobu Hotel offers an upscale experience that includes world-class mixology and a Japanese-inspired menu that reflects Nobu's renowned culinary excellence. Visitors can indulge in signature Nobu cocktails, with the "Nobu Sidecar" being a particular highlight, showcasing the mixologists' prowess in creating a modern twist on classic drinks or exotic plates like Lobster Tempura Truffle Amazu or Wagyu Dumplings or Sliders. The rooftop also hosts a variety of special events, ranging from brunch to evening DJ sessions, offering an unmatched ambiance for both daytime and nighttime entertainment.
Neighborhood: Old Town
Hours:
• Monday–Thursday: 4:00 PM – 11:00 PM
• Friday: 12:00 PM – 1:00 AM
• Saturday: 11:00 AM – 2:00 AM
• Sunday: 11:00 AM – 9:00 PM
Reservations: Encouraged; reserved tables held for 15 minutes. Walk-ins accepted until capacity is reached.
Elevator Pitch: A colorful indoor/outdoor “tailgate party meets rooftop” venue with oversized games, picnic tables, and lively decor high above Old Town.
Utopian Tailgate, is known for its color! Located above the home of comedy—Second City, this bar offers an eclectic mix of games, colorful décor, and sweeping views of the Chicago skyline from its spacious terrace. Bring some friends to play from an array of entertainment options, including ping pong tables, bocce ball, and giant Jenga, setting the stage for an unforgettable outing. The bar's menu is a testament to creativity, featuring a diverse selection of cocktails that are as visually appealing as they are delicious. Ask about the Playpen Playdate cocktail that serves 6-8 friends!
Neighborhood: Logan Square
Hours:
• Monday–Thursday: 11:00 AM – 9:00 PM
• Friday: 11:00 AM – 11:00 PM
• Saturday: 10:00 AM – 11:00 PM
• Sunday: 10:00 AM – 9:00 PM
Reservations: Available for dining and bar areas.
Elevator Pitch: A bright, Tex-Mex inspired all-day bar & restaurant with a breezy rooftop patio, inventive margaritas, and social design flair in Logan Square.
Lonesome Rose graces two neighborhoods in Chicago with its relaxed, Texan-inspired ambiance. It offers indoor and outdoor spaces to relax, have fun, and enjoy the welcoming environment. At Lonesome Rose, the culinary and cocktail offerings stand out, featuring a blend of traditional American and Tex-Mex flavors with its extensive taco and burrito menu and its take on Southwest Chicken Empanadas. Take advantage of the rooftop patio and bar in Logan Square for an afternoon or evening of fun in one of the coolest neighborhoods in the city.
Looking for more tips, guides, and information about the Windy City? Check out our Chicago blog for things to do in Chicago at any time of the year.
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