Water Activities in Chicago, IL

Cruise Chicago’s waterways aboard a floating tiki bar with Sunday drink specials

Set sail on Chicago waters with a captain at the helm

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

Bring your group aboard a rented vessel with a 100GT Masters Captain

Explore Chicago River routes by kayak or stand-up paddleboard at your own pace

Paddle the Chicago River in a single or double kayak, from the Wild Mile toward downtown

Build foundational kayaking skills on calm Chicago River waters

Watch fireworks and Chicago sights from a floating tiki bar

Explore Chicago’s shoreline with an experienced captain

Learn essential sea kayaking skills with certified instructors

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

Tailor a private Chicago boat outing with an experienced captain

Learn paddleboard skills for calm-water adventures

Celebrate on a tiki-themed yacht with an open bar and Chicago skyline views

Put an expert captain at the helm of your boat

Set out on Lake Michigan with an experienced captain

Private 50-foot charter with two decks, a waterslide, and an open bar

Private river cruising with Bluetooth sound and beverage credits on longer charters

Sail Chicago’s skyline aboard an 80-foot tiki-chic yacht

Celebrate on an 80-foot yacht with an included open bar

Private yacht charter with an included open bar and skyline charter option

Cruise the Chicago River aboard a private floating tiki bar

Private Chicago river and lake charter with an included open bar

Cruise Chicago’s river and lake skyline aboard a private two-deck party boat