Best 88 things to do in Chicago, IL

Eat Chicago’s five classic dishes with VIP access in River North and Streeterville

Ride a foodie bus to restaurants seen in The Bear, with tastings along the way

Walk Pilsen for tacos, cocktails, and mural-filled streets

Eat a donut, then head up to the Willis Tower Skydeck

Walk the Chicago Loop to see hidden interiors and Millennium Park

Cruise the Chicago River on a private boat with local architecture stories

See Chicago landmarks by helicopter with a 5-passenger twin-engine aircraft

Fly over Chicago landmarks with a private helicopter for up to 3

Take the controls in a 30-minute helicopter intro flight

Step inside Chicago’s Art Deco buildings on a 2-hour Loop walk

Discover Chicago architecture and fireboat history on a guided river cruise.

Eat Chicago favorites as you walk past top landmarks with a guide

Explore Chicago with other solo travelers on a guided social adventure

Taste your way through Chicago’s West Loop with a local guide

Eat your way through Chicago’s Chinatown with 5 seated tastings

Cruise Chicago waters with up to 13 guests for a flexible three-to-four-hour outing