Water Activities in Chicago, IL

Explore Lake Michigan by boat, from Playpen outings to Chicago river cruises

2-hour happy hour cruise with skyline views and a full bar

Share a peaceful Lake Michigan sail with Chicago skyline views

Private Lake Michigan fishing with an expert crew

Paddle the Chicago River and learn downtown architecture in 3 hours

Paddle Chicago's lakefront with skyline views and basic instruction

Private Lake Michigan sailing with swimming, snacks, and a certified captain

Sail Lake Michigan for sweeping views of Chicago’s skyline

Watch Chicago fireworks on a 90-minute tiki bar cruise

Self-drive pontoon on the Chicago River with Navy Pier fireworks

See Chicago from the water aboard a former Navy tactical boat

Private 40' Sea Ray yacht rental in Chicago for up to 13

Bring your group aboard for a captain-led Chicago outing

Paddle Chicago River routes in a single or double kayak

Hire a Polish-speaking captain for your rented Lake Michigan boat

A quiet private weeknight sail with Chicago skyline views

Cruise Chicago’s lakefront for skyline and Navy Pier views

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

Sail Lake Michigan on a private weeknight cruise with sunset and skyline views

Speed across Lake Michigan with your own music and skyline views

Sail Chicago’s lakefront at sunset aboard a private 37-foot yacht

A private sail for proposals, photos, and a champagne toast

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

Watch Navy Pier fireworks from the water with Chicago skyline views