AIRBNB EXPERIENCES

Sightseeing activities in Cook County

Book unique activities hosted by local experts on Airbnb.

Top-rated sightseeing activities

View our most highly rated experiences, loved by guests.

4.88 out of 5 average rating, 304 reviews

Chicago'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.

4.97 out of 5 average rating, 315 reviews

Award-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.

4.99 out of 5 average rating, 174 reviews

Walkin' 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, 52 reviews

Ultimate 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.

5 out of 5 average rating, 60 reviews

Learn to fly a plane - Discovery Flight

With no experience required, we offer a rare chance to experience the thrill of flight, guided by an FAA-certified instructor. Weight limit of 190lbs. Subject to weather. No passengers

4.92 out of 5 average rating, 36 reviews

Chicago's Lakefront Neighborhoods Bike Tour

Ride through Chicago's North Side, finding quiet streets, city parks, and sunny beaches.

4.9 out of 5 average rating, 62 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!

4.86 out of 5 average rating, 57 reviews

Explore Chicago's skyline from the air

Take a flight over Chicago, including Lake Michigan, Navy Pier, Wrigley Field, and Willis Tower.

4.88 out of 5 average rating, 26 reviews

Chicago Gangsters and Food Tour

Taste iconic Chicago foods while walking through a Prohibition Era neighborhood.

4.96 out of 5 average rating, 236 reviews

See Chicago by bike

Ride through diverse neighborhoods, see historic sites, and admire architecture and art.

Latest Activities

Explore new local experiences, activities for everyone.

5 out of 5 average rating, 6 reviews

Skip the line Tour at Art Institute of Chicago

Start with exclusive early access, before the museum opens, and explore iconic galleries.

5 out of 5 average rating, 12 reviews

Family Food Bike Tour - Explore Top Foods & Sites

Pedal to iconic downtown sites while sampling classic Chicago favorites. This family-friendly adventure blends skyline views, rich stories, & delicious bites into one unforgettable kid-friendly tour.

4.99 out of 5 average rating, 174 reviews

Walkin' 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, 16 reviews

Ride in a limo through Chicago

Experience a 3-hour Chicago limo tour with bar hopping, iconic sightseeing, and local history. Enjoy alcohol, soft drinks, and champagne included for a seamless VIP group experience this summer

4.92 out of 5 average rating, 36 reviews