Water Activities in Deer Park, IL

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

Paddle the Chicago River and learn downtown architecture in 3 hours

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

Anchor at Chicago’s Playpen for swimming, skyline views, and a laid-back day on the water

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

Cruise Chicago’s lakefront for skyline and Navy Pier views

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

Pontoon time for fishing, lounging, and pets

Ride a new 2026 Yamaha cruiser along Chicago's lakefront

See Chicago landmarks from the water on a private sightseeing outing

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

Private Chicago river and lake charter with an included open bar

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

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

Fish, lounge, or bring your pet aboard a Lake Elizabeth pontoon

Speed across Lake Michigan with your own music and skyline views

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

Photograph Chicago's skyline from a US Navy-built boat

Cruise the Chicago River for skyline views and Riverwalk sights

A spacious pontoon with a tiki bar, sound system, and swim ladder

Sail Lake Michigan for Chicago skyline views and Navy Pier fireworks

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

Gather your group for a spacious tiki barge day on Lake Elizabeth

Sail Chicago’s lakefront on a private charter with time to swim and relax