Best 209 things to do in Wilmette, IL

Taste Chicago classics and discover the stories behind the city’s signature dishes

Walk Chicago Chinatown and taste dishes from five Chinese regions

Pedal Chicago’s top sights while tasting pizza, hot dogs, and Italian beef

Bike Chicago’s lakefront parks and skyline highlights with a guide

Bike Chicago’s North Side neighborhoods and lakefront in 3 hours

Paddle Lake Michigan from Ohio Street Beach for two hours

Rent a bike by Chicago’s Lakefront Trail with maps, helmet, lock, and easy access near Navy Pier

Rent a bike for 24 hours near the Lakefront Trail and Navy Pier

Rent a bike near the Lakefront Trail and Navy Pier—return it by shop closing

Rent a bike for 4 hours steps from Navy Pier and the Lakefront Trail

Paddle Lake Michigan for Chicago skyline views

Private 1962 vintage motorboat cruise on the Chicago River for up to 6 guests

Cruise Chicago’s waterfront with a professional crew and private gathering spaces

Celebrate on the Gypsy Spirit along Chicago’s waterfront

Sail Chicago’s lakefront on a private yacht with a captain, swimming and music on board

Private Lake Michigan sailing with swimming, snacks, and a certified captain

Sail Chicago’s lakefront at sunset aboard a private 37-foot yacht

A private sail for proposals, photos, and a champagne toast

Design your own Chicago lakefront day aboard Soulshine

Ride a new 2026 Yamaha cruiser along Chicago's lakefront

Make your Chicago arrival in a Tesla Cybertruck

Taste four pizza styles on a 3-hour downtown Chicago walk

Trace Chicago’s Prohibition history across four neighborhood speakeasies

Explore Chicago's Prohibition era through stories of class, nightlife, and rebellion