Best 301 things to do in Chicago, IL

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

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

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

Charter a private 38' yacht on Lake Michigan for up to 13 guests

Anchor at Chicago’s Playpen for swimming, skyline views, and a laid-back day on the water

Cruise about two miles offshore for wide-open Chicago sunset views

Speed across Lake Michigan with your own music and skyline views

Set your own pace on a private Chicago yacht cruise

Double-decker catamaran for private entertaining and water views