Best 184 things to do in Chicago, IL

Fly over Chicago landmarks with a private helicopter for up to 3

Take the controls in a 30-minute helicopter intro flight

Watch Chicago fireworks from a floating tiki bar with a full onboard bar

Walk downtown Las Vegas and sample donuts and churros in 2 hours

Taste your way through downtown Boston on a private donut walk

Parasail up to 500 feet above Lake Michigan for skyline views

Discover Chicago architecture and fireboat history on a guided river cruise.

Live Electric Brew jams aboard a historic Chicago fireboat

Live stand-up, touring comedians, and skyline views aboard a historic fireboat

Explore Chicago with other solo travelers on a guided social adventure

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

Visit four Chicago pizzerias and compare four pizza styles by bus

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

Ride a foodie bus to restaurants seen in The Bear, with tastings along the way

Cruise Chicago waters with up to 13 guests for a flexible three-to-four-hour outing

Host a private Chicago event with open-air decks and a professional crew