Best results for Water Activities in Chicago, IL

Paddle Chicago River routes in a single or double kayak

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

Learn essential sea kayaking skills with certified instructors

Learn paddleboard skills for calm-water adventures

Private yachting for celebrations, family gatherings, and corporate outings

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

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

Private 37' Sea Ray Sundancer cruise for up to 13 guests

Cruise on a 46 ft Sea Ray Express with up to 13 guests

Cruise Chicago by private boat on a 50 ft Sea Ray Sundancer, up to 13 guests

Host a private celebration aboard a Hamptons-inspired catamaran

Celebrate, cruise, and swim aboard a 52-foot Sea Ray

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

Set your own pace on a private Chicago yacht cruise

Ride a Yamaha Waverunner with Chicago skyline views

Ride a Yamaha jet ski across Lake Michigan with views of Chicago’s skyline

Paddle Lake Michigan with Chicago skyline views

Paddle Chicago's lakefront with skyline views and basic instruction

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

Set sail aboard a 50' Sea Ray with a kitchen, bathrooms, and Sonos audio

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

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

Sail Lake Michigan for Navy Pier fireworks views on a private charter