things to do in Oak Park, IL

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

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

Set sail on Chicago waters with a captain at the helm

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

Explore Chicago’s shoreline with an experienced captain

Tailor a private Chicago boat outing with an experienced captain

Put an expert captain at the helm of your boat

Set out on Lake Michigan with an experienced captain

Discover Chicago architecture and fireboat history on a guided river cruise.

2-hour happy hour cruise with skyline views and a full bar

Live Electric Brew jams aboard a historic Chicago fireboat

Live stand-up, touring comedians, and skyline views aboard a historic fireboat

Sail Lake Michigan with Chicago skyline views

Share a peaceful Lake Michigan sail with Chicago skyline views

A quiet private weeknight sail with Chicago skyline views

Sail Lake Michigan on a private weeknight cruise with sunset and skyline views

Private Lake Michigan fishing with an expert crew

Cruise offshore from Navy Pier for fireworks and skyline views

Sail Chicago’s lakefront on a private yacht with a captain, swimming and music on board

Private Lake Michigan sailing with swimming, snacks, and a certified captain

Sail Chicago’s lakefront at sunset aboard a private 37-foot yacht