Best results for Water Activities in Chicago, IL

Celebrate on the Gypsy Spirit along Chicago’s waterfront

Design your own Chicago lakefront day aboard Soulshine

Ride a new 2026 Yamaha cruiser along Chicago's lakefront

Sail Lake Michigan for sweeping views of Chicago’s skyline

See Chicago’s skyline from Lake Michigan on an evening sail

Watch Navy Pier fireworks from the water with Chicago skyline views

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

Cruise Chicago by private 47 ft yacht with space for up to 12 guests

Cruise the Chicago River for 2 hours on a private, self-drive pontoon

Take the wheel on a 22 ft pontoon cruise on the Chicago River

Ride Lake Michigan with downtown Chicago views

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

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

Paddle the Chicago River and learn downtown architecture in 3 hours

Paddle the Chicago River past the Wild Mile and downtown skyline

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

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

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

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 paddleboard skills for calm-water adventures

Paddle Goose Island and downtown as Chicago lights reflect on the river

Private yachting for celebrations, family gatherings, and corporate outings