Best 209 things to do in Wilmette, IL

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

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

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

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

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

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

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

Ride a Yamaha Waverunner with Chicago skyline views

Taste your way through Chicago’s West Loop with a local guide

Eat Chicago’s five classic dishes with VIP access in River North and Streeterville

Ride a foodie bus to restaurants seen in The Bear, with tastings along the way