Water Activities in Chicago, IL

Private 1962 vintage motorboat cruise on the Chicago River for up to 6 guests

Cruise the Chicago River for skyline views and Riverwalk sights

Private yachting for celebrations, family gatherings, and corporate outings

Cruise Chicago’s lake and river on a historic fireboat with docent-led stories

Cruise Chicago’s waterfront with a professional crew and private gathering spaces

Charter a 47’ Carver yacht with kitchen, bathrooms, and Bluetooth audio

Private 6–8 hour fishing charter for up to 6 on Lake Michigan

Spread out with a spacious cockpit and two private staterooms

See Chicago’s illuminated skyline from two waterfront perspectives

Private Sea Ray yacht charter on Lake Michigan with 3–8 hour options

Enjoy a Chicago charter with a USCG-licensed captain and 15+ years of experience

Celebrate on the Gypsy Spirit along Chicago’s waterfront

Set the mood on board with your own food, drinks and music

Discover Chicago’s darker history from the river

Hire a Chicago captain and cruise to the Playpen, Monroe Harbor, or the river

Cruise Lake Michigan with a full kitchen, two bathrooms, and skyline views

Float through Chicago’s skyline on a festive fall hayride

Cruise a 47-foot Carver with space to relax, dine, and play your music

Relax together with a flybridge lounge, wide walkways, and onboard music

Sail Lake Michigan for Chicago skyline views and Navy Pier fireworks

Hire a US Coast Guard licensed captain for your Chicago boat day

Make your Chicago celebration a private day or night on the water

Cruise the water with a captain for relaxed outings, playpen visits or evening fireworks

Set your own pace on a private Chicago yacht cruise