Best 301 things to do in Chicago, IL

Discover armadillo behavior and environmental importance

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

Take the controls in a 30-minute helicopter intro flight

Learn About Winemaking in the Heart of Chicago

Watch fireworks and Chicago sights from a floating tiki bar

Watch Chicago fireworks on a 90-minute tiki bar cruise

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

Follow Chicago’s movie trail with a local actor guide

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

See Chicago fireworks from a floating tiki bar on Lake Michigan

Parasail up to 500 feet above Lake Michigan for skyline views

Follow a festive downtown trail of landmark trees, traditions, and indoor holiday displays

Private river cruising with Bluetooth sound and beverage credits on longer charters

Walk through Chicago scenes from Ferris Bueller, The Dark Knight, and more

Taste Chicago classics while exploring the city's landmark-filled streets

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

Live Electric Brew jams aboard a historic Chicago fireboat

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

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

Cruise Lake Michigan on a historic fireboat for Navy Pier fireworks views

Explore Chicago through social adventures with fellow solo travelers

Taste four Chicago pizza styles on a guided West Loop walk

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