Water Activities in Naperville, IL

Set your own pace on a private Chicago yacht cruise

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

Double-decker catamaran for private entertaining and water views

Cruise with Captain Rudy at 31st Street Harbor

Cruise Chicago by private boat with an experienced captain

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

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

Explore Chicago’s waters with an experienced local captain

Put an expert captain at the helm of your boat

A local captain for your Chicago day on the water

Celebrate aboard a restored classic with three levels and open-air spaces