
AIRBNB EXPERIENCES
Things to do in Chicago
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Top-rated activities
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4.67 out of 5 average rating, 12 reviews360 Chicago - General Admission Entry
Ascend 1,000 ft in a 40-second elevator ride to soak in panoramic views of Chicago. Explore exhibits on Chicago's vibrant culture, upgrade to the TILT, and enjoy a drink at the CloudBar.
4.91 out of 5 average rating, 447 reviewsChicago Underground Pedway & Secret Interiors Tour
Explore Chicago's underground Pedway: hidden corridors of stained glass, quirky stories, and many secrets both underground and above, with stunning architecture and unexpected details.
4.88 out of 5 average rating, 314 reviewsChicago's Famous Foods & Top Attractions Walk Tour
Taste your way through Chicago on this award-winning Chicago Food & Walking Tour! Enjoy five iconic tastings—deep dish pizza, hot dogs, Italian beef, Garrett's popcorn, brownie—plus top attractions.
4.94 out of 5 average rating, 313 reviewsChinatown's Food & Culture Walking Tour in Chicago
Taste your way through Chicago’s Chinatown on this 1-mi award-winning Food & Culture Walking Tour! Enjoy 5 tastings—dim sum, chili chicken, lamb cumin, egg tarts, and more—plus tea & drink upgrades.
4.94 out of 5 average rating, 1276 reviewsDiscover Chicago's Dazzling Architecture Interiors
See the stunning and often overlooked architecture interiors of downtown Chicago on Chicago original and best interiors tour!
4.93 out of 5 average rating, 944 reviewsPaint your own street art at Studio WIP
Unleash your creativity at this art hub in Chicago’s Uptown neighborhood. Local artists will show you how to spray-paint using insider tricks, and you’ll leave with finished art. Beginners welcome.
4.99 out of 5 average rating, 176 reviewsWalkin' With Colin Chicago Tour du Jour
A sensational journey through the history, mystery, comedy and tragedy of The Windy City.
4.94 out of 5 average rating, 273 reviewsChicago in a Day: Food, History & Landmarks
Walk through Chicago’s vibrant heart, exploring iconic architecture and tasting classic local flavours like deep-dish, hot dogs, and Italian beef along the way.
4.94 out of 5 average rating, 54 reviewsUltimate City Bike Tour of Top Chicago Attractions
Ride Chicago’s top attractions—Millennium Park, Buckingham Fountain, Navy Pier, Museum Campus & Lakefront. Enjoy skyline views & fascinating stories on an easy bike tour through the heart of the city.
4.97 out of 5 average rating, 317 reviewsAward-winning Bikes, Bites & Views Tour - Adults
Ride through Chicago, tasting deep dish pizza, hot dogs, brownies & local beers (with VIP upgrade). This adults-only food/bike tour has day routes to Wrigley Field & night routes of top attractions.
Latest Activities
Explore new local experiences, activities for everyone.
New place to stayCapture city memories with a personal photoshoot
Get a private photoshoot session at some of the city's best photo spots with a local Chicagoan photographer. Guaranteed Insta-worthy! *if you don’t see the date/time you’re looking for, message me!
New place to stayColor Factory Chicago - Ticket Only
Voted USA Today's Best Immersive Experience in 2024 and 2025, get ready to take an interactive journey through 12+ immersive art exhibits as stunning as they are colorful.
New place to stayThe Chicago Gauntlet: Food, Culture & Hidden Bars
In one evening, we’ll move through multiple neighborhoods, taste iconic Chicago bites, cruise skyline routes at sunset, and finish with hidden bar energy — all in a small group, in comfort.
New place to stayFreestyle Ceramic and Tufting
we believe creativity has no limits. Our studio is more than just a place to make pottery—it's a place to explore, learn, connect, and express yourself through the timeless art of ceramics. =)
New place to stayMost Popular Rug Tufting
custom make your own rug . from design , color , tufting to finish or pick one from our collection
New place to stayChoose Your Own Art Adventure @ the Art Institute
Intimate tours where you choose your own art adventure from expertly curated mini-tours. Immerse yourself in celebrated masterpieces with storytelling, history, and a grand finale in the Modern Wing
5 out of 5 average rating, 1 reviewsMezcal Tasting Class Through Untold Stories
Explore a guided Mezcal tasting class featuring seasonal flavors with appetizers. Learn about the sacred agave and savor flavors of Mexico.
New place to stayCrates & Coffee: Chicago Vinyl Crawl Experience
Explore Chicago’s music culture through a vinyl and coffee experience. Learn to dig for records, visit local shops, and hear stories of house, soul, and R&B. Stop for coffee and discover new sounds.
New place to stayInsider Route 66 Experience - Bilingual Tour Guide
Explore five hours of Middle America on the Mother Road! We start in Chicago and end in a historic winery! My insider knowledge is exactly what you need to make the most out of your Rt. 66 experience!
New place to stayPuerto Rican Food and Culture Tour in Humbolt Park
Immerse yourself in Chicago’s Puerto Rican community on a guided tour. Savor authentic dishes, explore vibrant murals, and enjoy traditional sweets and drinks.
Where do locals hang out in Chicago?
Pilsen (Lower West Side)
Chicago has long attracted writers, musicians, artists, and other creatives. Take in the arts, dining, and nightlife of the Pilsen neighborhood to see firsthand where the people who live here go out to enjoy life’s finer things in areas such as the Chicago Arts District, home to National Museum of Mexican Art, the Chicago Art Department, and more.
Hyde Park (South Side)
For a low-key day, head to the South Side neighborhood of Hyde Park where you’ll find people roaming tree-lined boulevards en route to indie bookstores, under-the-radar museums, and the University of Chicago to enjoy prolific Gothic architecture.
Logan Square
Want the Wicker Park hip factor without the brunch wait lines? Check out the Logan Square neighborhood. Here you can get your fix of Michelin-rated restaurants and cocktail bars before cozying up indoors at the Logan Theatre for an indie flick. On Sundays, take a stroll through the farmers’ market that operates all year. For those who want to get hands-on, try making your own street art in a nearby studio with local artists.
What do locals eat in Chicago?
When it comes to what locals eat in Chicago, it can depend on who you ask. No one is going to tell you not to grab a slice of deep-dish pizza or a hot dog, but also that there’s more to savor than these classics. Dry-aged steaks on the Loop, West African cuisine in Bronzeville, tacos in Little Village, pierogies downtown: the food here a reflection of this multicultural Midwestern city.
The Andersonville and Argyle neighborhoods are a must when it comes to food. On Argyle Street, a cluster of Southeast Asian restaurants offer some of the best Asian food in all of the city, meanwhile in Andersonville you’ll find Turkish, Lebanese, and Swedish eats.
What is unique about Chicago’s architecture?
Chicago’s unique architecture is the result of an otherwise tragic historical event: the Great Fire of 1871 which destroyed most of the downtown buildings. By the 1880s, a group of architects called the Chicago School began to promote a new way of building known as “commercial-style” architecture characterized by steel-frame construction and large plates of glass. The result? The world got the first modern skyscraper, the Home Insurance Building, in 1885. Since then, Chicago has always been a world leader in design, with notable styles such as Chicago bungalows, two-flats, grandiose graystones, and Polish cathedrals.
Whether it’s your first visit to Chicago, or you’re a lifelong resident, there are plenty of fun architecture-related activities (both indoors and outdoors) to experience this iconic piece of Chicago history firsthand.
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