Water Activities in Chicago, IL

Private Chicago cruising with a kitchen, bathroom and Bluetooth sound

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

Cruise Chicago’s waterfront with a certified EMT captain

Cruise Chicago with a flexible captain for your 3–4 hour charter

Cruise offshore from Navy Pier for fireworks and skyline views

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

Paddle the Chicago River after dark with city lights and stories from your guide

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

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

Island tunes, skyline views, and a full bar on the Chicago River

90-minute group sail for Navy Pier fireworks and Chicago skyline views

Ride Lake Michigan with downtown Chicago views

Parasail up to 500 feet above Lake Michigan for skyline views

Hire a Chicago captain for a Lake Michigan outing

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

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

Pilot a 2-person Craig Cat and cruise the Chicago River skyline

Choose your paddlecraft for a self-guided outing on the water

Take in Chicago’s skyline from a floating tiki bar with a full bar on board

Jet ski on Lake Michigan with skyline and Navy Pier views

See Chicago by water from a floating tiki bar with Sunday drink specials

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

Paddle past the Wild Mile and Chicago's skyline in a single or double kayak