Bert surprises 2 friends with an all-expenses-paid dream adventure to the Windy City. While in Chicago, our adventurers experiment with jetpacks, roll like '30s gangsters and shred invisible guitars.Go to Episode
Notorious Chicago gangster Hymie Weiss was gunned down on the steps of this iconic gothic-style cathedral in Chicago.
730 N. State St
Chicago, IL 60611
Flyboarding is the latest and greatest in water sports Learn what it’s like to fly by strapping on a water-propelled jet pack -- attached to a jet ski -- and using hand-operated controls to soar above the water.
Located on Navy Pier, the Red Witch is Chicago’s tallest -- and only -- wooden ship. If Chicago is the Windy City, why not put some of that wind to use? A ride on the Red Witch is an authentic sailing experience.
800 E Waldron Ave Dock J
Chicago, IL 60605
Untouchable Tours offers a full tour of Chicago’s gangster past. Gangsters gained notoriety on Chicago’s streets during the 1920s and left behind a trail of chaos, terror and brutality.
10429 S Prospect Ave
Chicago, IL 60643
The Biograph Theater is the location where notorious mobster John Dillinger was gunned down. The theater is one of the many unique stops on Chicago’s Untouchable Tours.
2433 N Lincoln Ave
Chicago, IL 60614
The Windy City Rollers is Chicago’s premiere all-female flat track derby league. Roller Derby is currently in consideration as an Olympic sport and provides action-packed entertainment for the whole family.
525 S Racine Ave
Chicago, IL 60607
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