Best results for Tours And Adventures in Chicago, IL

Build foundational kayaking skills on calm Chicago River waters

Paddle Goose Island and downtown as Chicago lights reflect on the river

Cruise Chicago’s lakefront in an exotic vehicle with skyline and landmark views

Cruise Chicago on a 10-mile Lamborghini Urus ride

See Chicago landmarks from the back seat of a Rolls-Royce with a private driver

Private chauffeur service with luxury vehicle requests in Chicago

Private chauffeur service with luxury and exotic vehicle options

Travel privately in a chauffeur-driven Rolls-Royce Phantom

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

Discover Lincoln Park’s nature and history with a local guide

Cruise the Chicago River for skyline views and Riverwalk sights

Relax together with a flybridge lounge, wide walkways, and onboard music

Private cruising for relaxed gatherings and celebrations

Make your Chicago celebration a private day or night on the water

Private yachting for celebrations, family gatherings, and corporate outings

Enjoy a Chicago charter with a USCG-licensed captain and 15+ years of experience

Hire a Polish-speaking captain for your rented Lake Michigan boat

Hire a Chicago captain and cruise to the Playpen, Monroe Harbor, or the river

Hire a US Coast Guard licensed captain for your Chicago boat day

Cruise the water with a captain for relaxed outings, playpen visits or evening fireworks

Captain for hire on Lake Michigan, with payment options and holiday rates

Cruise with Captain Rudy at 31st Street Harbor

Hire a Chicago captain for a Lake Michigan outing

Cruise Chicago by private boat with an experienced captain