Best 252 things to do in Oakbrook Terrace, IL

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

Make your Chicago arrival in a Tesla Cybertruck

Sail Lake Michigan for sweeping views of Chicago’s skyline

Sail Lake Michigan with live blues from Michael Charles and his band

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

Explore historic prison spaces at your own pace

Cruise the Chicago River for skyline views and Riverwalk sights

Sail Lake Michigan on a private day charter with skyline views

Trace Chicago's skyscraper story with a donut tasting

Step inside Chicago Loop landmarks and trace the evolution of its skyline