Best results for Water Activities in Oakbrook Terrace, IL

Sail Lake Michigan at sunset for Chicago skyline views from the water

Build practical sailing skills aboard a 26-foot Chris-Craft on Lake Michigan

Sail Chicago's lakefront from Museum Row to Navy Pier at sunset

Paddle the Fox River at your own pace with an easy dam portage

A beginner-friendly Fox River float with no portages

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

Sail Chicago’s lakefront on a private yacht with a captain, swimming and music on board

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

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

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

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

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 and swim aboard a spacious Sea Ray with room to lounge