Best 184 things to do in Chicago, IL

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

Sail Lake Michigan with Chicago skyline views

Share a peaceful Lake Michigan sail with Chicago skyline views

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

Private Lake Michigan fishing with an expert crew

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

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

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

Eat a donut, then head up to the Willis Tower Skydeck

Walk the Chicago Loop to see hidden interiors and Millennium Park

Cruise the Chicago River on a private boat with local architecture stories

See Chicago landmarks by helicopter with a 5-passenger twin-engine aircraft