Best results for Chicago Illinois

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

Taste Lincoln Square’s European roots and Silk Road flavors on foot

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

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

Private Chicago cruising with a kitchen, bathroom and Bluetooth sound

Charter a private 38' yacht on Lake Michigan for up to 13 guests

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

Trace Chicago's skyscraper story with a donut tasting

Step inside Chicago Loop landmarks and trace the evolution of its skyline

Private skyline cruise with a local perspective

Meet Farm Animals and Native Wildlife Across Five Acres

Discover armadillo behavior and environmental importance

Fly over Chicago landmarks with a private helicopter for up to 3