Best results for Tours And Adventures in Chicago, IL

Bike Miami Beach and sample local food with a guide

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

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

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

Sail Chicago’s lakefront on a private yacht with a captain, swimming and music on board

Private Lake Michigan sailing with swimming, snacks, and a certified captain

Sail Chicago’s lakefront at sunset aboard a private 37-foot yacht

A private sail for proposals, photos, and a champagne toast

Cruise Chicago’s waterfront with a professional crew and private gathering spaces

Celebrate on the Gypsy Spirit along Chicago’s waterfront

Cruise the Chicago River for 2 hours on a private, self-drive pontoon

Take the wheel on a 22 ft pontoon cruise on the Chicago River

Explore Chicago's past with a private guide and museum admission included

Explore Chicago Chinatown on a 2026 USA Today 10Best History Tour winner

Cruise Chicago by private 47 ft yacht with space for up to 12 guests

Cruise Chicago’s river in a vintage 1950s Milo Craft

Paddle the Chicago River and learn downtown architecture in 3 hours