Best 308 things to do in Wilmette, IL

Night kayak tour to watch Navy Pier fireworks

Jet ski on Lake Michigan with skyline and Navy Pier views

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

Visit four Chicago pizzerias and compare four pizza styles by bus

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

Parasail up to 500 feet above Lake Michigan for skyline views

Taste four Chicago pizza styles on a guided West Loop walk

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

Explore Chicago through social adventures with fellow solo travelers

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

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

Learn About Winemaking in the Heart of Chicago

See Chicago by water from a floating tiki bar with Sunday drink specials

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

Sail Lake Michigan with live blues from Michael Charles and his band

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

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

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

See Chicago fireworks from a floating tiki bar on Lake Michigan

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