Best 367 things to do in Wood Dale, IL

Cruise Chicago’s lake and river on a historic fireboat with docent-led stories

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

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

Celebrate on the Gypsy Spirit along Chicago’s waterfront

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

Design your own Chicago lakefront day aboard Soulshine

Ride a new 2026 Yamaha cruiser along Chicago's lakefront

Make an entrance in a 2024 Tesla Cybertruck for your next Chicago outing

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

Relax together with a flybridge lounge, wide walkways, and onboard music

Set your own pace on a private Chicago yacht cruise

Double-decker catamaran for private entertaining and water views

Private yachting for celebrations, family gatherings, and corporate outings

Enjoy a Chicago charter with a USCG-licensed captain and 15+ years of experience

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

Hire a Chicago captain and cruise to the Playpen, Monroe Harbor, or the river

Hire a US Coast Guard licensed captain for your Chicago boat day

Cruise the water with a captain for relaxed outings, playpen visits or evening fireworks