Best 340 things to do in Wheaton, IL

Explore Chicago through social adventures with fellow solo travelers

Pedal through Chicago neighborhoods while tasting pizza, hot dogs, brownies, and optional beer pairings

Walk South Beach and sample local favorites with a guide

Bike and taste your way through Miami Beach’s Art Deco streets and local eats

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

Cruise Chicago’s lake and river on a historic fireboat with docent-led stories

2-hour happy hour cruise with skyline views and a full bar

Relax together with a flybridge lounge, wide walkways, and onboard music

Set your own pace on a private Chicago yacht cruise

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

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