Trip Flip: Chicago Pictures

Bert surprises 2 friends with an all-expenses-paid dream adventure to the Windy City.

Episode: Chicago

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Bert and our Chicago adventurers, Mike and Dave, toast after spending their first day of the trip at the Gangster Museum.

A view of the Chicago skyline behind the Red Witch. Located on Navy Pier, the Red Witch is Chicago’s tallest -- and only -- wooden ship.

The crew of the Sea Dog, a famous tour of Chicago by water, prepares to take the group out on a private tour.

Dave attempts to flyboard while in Chicago.

Bert screams with joy after his first flyboarding experience.

A stone lion stands tall outside of the Lincoln Park Zoo.

A must-try when visiting Chicago, Al's Italian beef sandwich lays out on display.

Bert and the adventurers ride the Ferris wheel at Chicago's Navy Pier.

Mike poses with the Windy City Rollers after getting his butt kicked on the track.

Dave and Mike try out their best gangster poses while enjoying their time at the Gangster Museum.

Bert, Mike and Dave pose in front of the Chicago skyline after a successful Trip Flip.