Best 301 things to do in Chicago, IL

Private chauffeur service with luxury and exotic vehicle options

Travel in a Rolls-Royce with private chauffeur service

Take the wheel of a V12 luxury sedan with a star-lit ceiling

Experience Chicago in the spacious, V-12-powered 2021 Phantom

Taste Mexican cuisine and discover Pilsen’s mural-covered streets

Eat Chicago’s five classic dishes with VIP access in River North and Streeterville

Ride a foodie bus to restaurants seen in The Bear, with tastings along the way

Eat your way through Chicago’s Chinatown with 5 seated tastings

Discover Lincoln Park’s nature and history with a local guide

Walk Logan Square murals and learn the artists behind them

Cruise the Chicago River for skyline views and Riverwalk sights

Sail Lake Michigan on a private day charter with skyline views

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

Private cruising for relaxed gatherings and celebrations

Paddle Lake Michigan with Chicago skyline 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

Captain for hire on Lake Michigan, with payment options and holiday rates

Cruise with Captain Rudy at 31st Street Harbor

Hire a Chicago captain for a Lake Michigan outing