AIRBNB EXPERIENCES

Outdoor activities in Chicago

Book unique activities hosted by local experts on Airbnb.

Latest Activities

Explore new local experiences, activities for everyone.

60 min Chicago architecture cruise from Navy Pier

Cruise Chicago’s river and marvel at iconic skyscrapers with engaging expert stories on this 60-minute Architecture adventure.

New place to stay

75 min Chicago architecture cruise - Michigan Ave

Cruise Chicago’s river and marvel at iconic skyscrapers with engaging expert stories on this 75-minute Architecture adventure.

5 out of 5 average rating, 1 reviews

75 min Chicago architecture cruise from Navy Pier

Cruise Chicago’s river and marvel at iconic skyscrapers with engaging expert stories on this 75-minute Architecture adventure.

New place to stay

90 min Chicago architecture cruise from Navy Pier

Cruise Chicago’s river and marvel at iconic skyscrapers with engaging expert stories on this 90-minute Architecture adventure.

New place to stay

Explore Chicago’s skyline from Lake Michigan

Enjoy unmatched views of Chicago’s skyline as you cruise Lake Michigan, soaking in iconic landmarks while learning local stories.

5 out of 5 average rating, 16 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.

4.92 out of 5 average rating, 37 reviews

Chicago's Lakefront Neighborhoods Bike Tour

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

4.95 out of 5 average rating, 63 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.