Best 203 things to do in Chicago, IL

Learn About Winemaking in the Heart of Chicago

Private 1962 vintage motorboat cruise on the Chicago River for up to 6 guests

Cruise Chicago’s lake and river on a historic fireboat with docent-led stories

2-hour happy hour cruise with skyline views and a full bar

Cruise Lake Michigan on a historic fireboat for Navy Pier fireworks views

Sample Chicago favorites while cycling through vibrant Near West Side neighborhoods on a fun 4-hour guided ride

Taste Wynwood favorites while exploring its murals and landmark streets

Walk Chicago’s must-see sights, including Millennium Park, in 2 hours

Bike Miami Beach and sample local food with a guide

Walk Wynwood’s street art scene with Wynwood Walls entry included

Taste Cuban favorites and uncover Little Havana’s food, history and landmarks

Pedal through Chicago neighborhoods while tasting pizza, hot dogs, brownies, and optional beer pairings

Walk South Beach and sample local favorites with a guide

Taste Chicago classics and discover the stories behind the city’s signature dishes

Walk Chicago Chinatown and taste dishes from five Chinese regions

Pedal Chicago’s top sights while tasting pizza, hot dogs, and Italian beef

Bike Chicago’s lakefront parks and skyline highlights with a guide

Bike Chicago’s North Side neighborhoods and lakefront in 3 hours

Paddle Lake Michigan from Ohio Street Beach for two hours

Rent a bike by Chicago’s Lakefront Trail with maps, helmet, lock, and easy access near Navy Pier

Rent a bike for 24 hours near the Lakefront Trail and Navy Pier

Rent a bike near the Lakefront Trail and Navy Pier—return it by shop closing

Rent a bike for 4 hours steps from Navy Pier and the Lakefront Trail

Paddle Lake Michigan for Chicago skyline views