Best results for Chicago IL

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

Paddle Lake Michigan off Ohio Street Beach for an hour

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

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

Taste six authentic dishes while exploring Uptown’s immigrant stories and landmark architecture

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

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

Sail past the Chicago skyline on a 2-hour 21+ cruise with drinks for purchase and Thursday brewery or Friday live music

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

Explore Chicago with other solo travelers on a guided social adventure

Charter a 47 ft yacht to cruise the Chicago River or Lake Michigan with BYOB and skyline views

Captain your own pontoon on the Chicago River for two hours with training and life vests provided

Drive your own pontoon on the Chicago River with BYOB and a quick lesson

Taste Chicago's West Loop with guided stops at acclaimed eateries and artisan spots

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

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

Taste Vietnam, the Middle East, and Sweden while exploring Argyle and Andersonville with a guide