Best 301 things to do in Chicago, IL

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

Sample Chicago favorites while cycling through vibrant Near West Side neighborhoods on a fun 4-hour guided ride

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

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

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

Celebrate on the Gypsy Spirit along Chicago’s waterfront

Make an entrance in a 2024 Tesla Cybertruck for your next Chicago outing

Sail Lake Michigan for sweeping views of Chicago’s skyline

See Chicago’s skyline from Lake Michigan on an evening sail

Cruise the Chicago River for 2 hours on a private, self-drive pontoon

Take the wheel on a 22 ft pontoon cruise on the Chicago River

Explore Chicago's past with a private guide and museum admission included

Explore Chicago Chinatown on a 2026 USA Today 10Best History Tour winner

Walk Chicago Chinatown and taste dishes from five Chinese regions

Cruise Chicago by private 47 ft yacht with space for up to 12 guests