Best 198 things to do in Chicago, IL

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

Set your own pace on a private Chicago yacht cruise

Ride a Yamaha Waverunner with Chicago skyline views

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

Private 6–8 hour fishing charter for up to 6 on Lake Michigan

Sail Lake Michigan for Navy Pier fireworks views on a private charter

Sail Chicago's Playpen with a licensed captain and time to swim

Private sailboat time with Chicago skyline views

Watch the Chicago skyline glow from a private sailboat on Lake Michigan

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

Eat your way through Uptown’s immigrant neighborhoods in 2.5 hours

A quiet private weeknight sail with Chicago skyline views

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

Anchor at Chicago’s Playpen for swimming, skyline views, and a laid-back day on the water

Cruise Chicago’s lakefront for skyline and Navy Pier views

Cruise about two miles offshore for wide-open Chicago sunset views

Speed across Lake Michigan with your own music and skyline views

Cruise offshore from Navy Pier for fireworks and skyline views

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