things to do in Chicago, IL

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

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

Private cruising for relaxed gatherings and celebrations

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

Host a private celebration aboard a Hamptons-inspired catamaran

Spend a relaxed day on Lake Michigan with a licensed captain at the helm

Chart a captain-led Lake Michigan or Chicago River outing tailored to your plans

Host a private Chicago event with open-air decks and a professional crew

Celebrate, cruise, and swim aboard a 52-foot Sea Ray

Cruise Chicago with a safety-focused captain experienced in commercial fishing

Chicago Skyline Cruise With an Experienced Captain

Set sail on Chicago waters with a captain at the helm

Experienced licensed captain for your Chicago boat charter

Shape your Chicago boat day with an experienced local captain

U.S. Coast Guard-certified captain for your Lake Michigan charter

A captain for your Chicago boat charter

Experienced U.S. Coast Guard–licensed captain for your Sea Ray outing

Bring your group aboard a rented vessel with a 100GT Masters Captain