Tours And Adventures in Chicago, IL

Watch Chicago fireworks on a 90-minute tiki bar cruise

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

Celebrate on an 80-foot yacht with an included open bar

Cruise Chicago’s river and lake skyline aboard a private two-deck party boat

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

Sail Chicago’s skyline aboard an 80-foot tiki-chic yacht

Private yacht charter with an included open bar and skyline charter option

Island tunes, skyline views, and a full bar on the Chicago River

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

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

Private 50-foot charter with two decks, a waterslide, and an open bar

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

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

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

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

See holiday lights, market traditions, and Chicago's tree on a downtown stroll

Explore Chicago through social adventures with fellow solo travelers

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

Sail Lake Michigan for sweeping views of Chicago’s skyline

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