Best 122 things to do in Chicago, IL

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 Chicago pizza styles on a guided West Loop walk

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

Cruise out for Navy Pier fireworks with skyline views and bar service

90-minute group sail for Navy Pier fireworks and Chicago skyline views

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

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

Self-drive pontoon on the Chicago River with Navy Pier fireworks

Pilot a 2-person Craig Cat and cruise the Chicago River skyline

Paddle the Chicago River and learn downtown architecture in 3 hours

Night kayak tour to watch Navy Pier fireworks

Cruise Chicago on a 10-mile Lamborghini Urus ride

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

Eat your way through Chicago’s Chinatown with 5 seated tastings

Walk Pilsen for tacos, cocktails, and mural-filled streets

Charter a 48 ft Sea Ray Flybridge for up to 13 guests on Lake Michigan

Private Sea Ray yacht charter on Lake Michigan with 3–8 hour options

Private 37' Sea Ray Sundancer cruise for up to 13 guests