Water Activities in Chicago, IL

Sail Chicago’s lakefront on a private charter with time to swim and relax

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

Cruise with Captain Rudy at 31st Street Harbor

Double-decker catamaran for private entertaining and water views

Sail Lake Michigan with Chicago skyline views

Cruise Chicago by private boat with an experienced captain

Sail Lake Michigan at sunset for Chicago skyline views from the water

Build practical sailing skills aboard a 26-foot Chris-Craft on Lake Michigan

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

Private cruising for relaxed gatherings and celebrations

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

Sail Chicago's lakefront from Museum Row to Navy Pier at sunset

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

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

Experienced licensed captain for your Chicago boat charter

Shape your Chicago boat day with an experienced local captain

A captain for your Chicago boat charter

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