Best 124 things to do in Deerfield, IL

Walk Little Havana and taste classic Cuban bites in 3 hours

Explore Chicago with other solo travelers on a guided social adventure

Bike 13 miles through Chicago neighborhoods and sample pizza, hot dogs, and brownies

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

Walk downtown Chicago and sample deep-dish pizza, Italian beef, a classic hot dog, and dessert

Walk Chicago Chinatown and taste dishes from five Chinese regions

Bike 10 miles as you sample Chicago staples and see top sights

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 off Ohio Street Beach for an hour

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

Taste Chicago pizza on a guided bus tour with 4 neighborhood stops

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

Walk Chicago’s Pedway and spot hidden details in the Loop

Walk the Loop to see Chicago’s hidden interior architecture

Walk Chicago’s dark history in 2 hours, from gangsters to ghost lore

Step inside Chicago’s Art Deco buildings on a 2-hour Loop walk

Private 3-hour sail to view Navy Pier fireworks with a USCG-certified captain included