Best results for Water Activities in Chicago, IL

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

Cruise Chicago’s lakefront for skyline and Navy Pier views

Speed across Lake Michigan with your own music and skyline views

Private 40' Sea Ray yacht rental in Chicago for up to 13

Private Chicago cruising with a kitchen, bathroom and Bluetooth sound

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

Cruise and swim aboard a spacious Sea Ray with room to lounge

See Chicago fireworks from a floating tiki bar on Lake Michigan

Watch Chicago fireworks on a 90-minute tiki bar cruise

Watch Chicago fireworks from a floating tiki bar with a full onboard bar

Parasail up to 500 feet above Lake Michigan for skyline views

Cruise Lake Michigan on a historic fireboat for Navy Pier fireworks views

Private 3-hour sail to view Navy Pier fireworks with a USCG-certified captain included

Self-drive pontoon on the Chicago River with Navy Pier fireworks

Jet ski on Lake Michigan with skyline and Navy Pier views

Cruise Chicago’s river in a vintage 1950s Milo Craft

Paddle Lake Michigan’s shoreline for city views and guided instruction

Night kayak tour to watch Navy Pier fireworks

Learn essential sea kayaking skills with certified instructors

Cruise Chicago waters with up to 13 guests for a flexible three-to-four-hour outing

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

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