Yacht Charters in Chicago, IL

Private Chicago river and lake charter with an included open bar

Celebrate on a tiki-themed yacht with an open bar and Chicago skyline views

Design your own Chicago lakefront day aboard Soulshine

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

Celebrate on the Gypsy Spirit along Chicago’s waterfront

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

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 Chicago by private boat with an experienced captain

Hire a seasoned Lake Michigan captain with 40+ years of experience

Charter a 48 ft Sea Ray Flybridge for up to 13 guests on Lake Michigan

Hire a captain for 3–4 hours, with flexible languages and a safety-first focus

Cruise on a 46 ft Sea Ray Express with up to 13 guests

Cruise Chicago by private boat on a 50 ft Sea Ray Sundancer, up to 13 guests

Hire a Lake Michigan captain familiar with Chicago’s boating hot spots