Best 301 things to do in Chicago, IL

Private Sea Ray yacht charter on Lake Michigan with 3–8 hour options

Cruise Lake Michigan with a full kitchen, two bathrooms, and skyline views

Ride a Yamaha jet ski across Lake Michigan with views of Chicago's skyline

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 Chicago skyline views and Navy Pier fireworks

Sail Chicago’s lakefront on a private charter with time to swim and relax

Sail Lake Michigan with Chicago skyline views

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

Choose your paddlecraft for a self-guided outing on the water

Explore Chicago River routes by kayak or stand-up paddleboard at your own pace

Learn paddleboard skills for calm-water adventures

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

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

Cruise Chicago’s lakefront for skyline and Navy Pier views

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

Private Chicago cruising with a kitchen, bathroom and Bluetooth sound

Cruise and swim aboard a spacious Sea Ray with room to lounge

See Chicago's northwest suburbs and the Fox River from the air

Meet Farm Animals and Native Wildlife Across Five Acres