Best results for Tours And Adventures in Chicago, IL

See Chicago landmarks from the water on a private sightseeing outing

Photograph Chicago's skyline from a US Navy-built boat

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

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

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

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

Meet Farm Animals and Native Wildlife Across Five Acres

Take in Chicago’s skyline from a floating tiki bar with a full bar on board

See Chicago by water from a floating tiki bar with Sunday drink specials

Cruise Chicago’s waterways aboard a floating tiki bar with Sunday drink specials

Watch fireworks and Chicago sights from a floating tiki bar