AIRBNB EXPERIENCES

Things to do in Chicago

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Top-rated activities

View our most highly rated experiences, loved by guests.

4.96 out of 5 average rating, 57 reviews

Solve a murder while hearing true crime stories.

Play detective while exploring Chicago neighborhoods with a historian and improviser.

4.94 out of 5 average rating, 1223 reviews

Discover Chicago's Dazzling Architecture Interiors

See the stunning and often overlooked architecture interiors of downtown Chicago on Chicago original and best interiors tour!

4.94 out of 5 average rating, 896 reviews

Street Art Workshop

Unleash your creativity with local artists using lettering, stencils, and cap techniques.

4.96 out of 5 average rating, 300 reviews

Award-winning Bikes, Bites & Brews Tour - Adults

Ride through Chicago, tasting deep dish pizza, hot dogs, brownies, and local beers.

4.99 out of 5 average rating, 161 reviews

Walkin' With Colin Chicago Tour du Jour

A sensational journey through the history, mystery, comedy and tragedy of The Windy City.

4.91 out of 5 average rating, 357 reviews

Chicago 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.

4.95 out of 5 average rating, 273 reviews

Chinatown's Food & Culture Walking Tour in Chicago

Sample culinary delights from 5 Chinese regions while knowing the history and culture.

4.88 out of 5 average rating, 279 reviews

Chicago's Famous Foods & Top Attractions Walk Tour

Feast on Chicago culinary legends and explore iconic landmarks in just three hours.

4.9 out of 5 average rating, 61 reviews

Get Inside Stunning Art Deco Interiors of the '20s

Return to the glitz and glam of the 1920s through its stunning Art Deco interiors!

4.83 out of 5 average rating, 132 reviews

Explore Chicago's hidden bars

Discover hidden gems in Chicago's bar scene. Enjoy drinks and a great atmosphere.

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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