Chicago

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.

From This Episode

Bert, David and Mike
Bert, David and Mike

Bert, David and Mike

Bert and our Chicago adventurers, Mike and Dave, toast after spending their first day of the trip at the Gangster Museum. 960 1280

  

Red Witch

Red Witch

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. 960 1280

  

Sea Dog Crew

Sea Dog Crew

The crew of the Sea Dog, a famous tour of Chicago by water, prepares to take the group out on a private tour. 960 1280

  

Flyboarding in Chicago

Flyboarding in Chicago

Dave attempts to flyboard while in Chicago. 960 1280

  

First Time Flyboarder

First Time Flyboarder

Bert screams with joy after his first flyboarding experience. 960 1280

  

Lincoln Park Zoo

Lincoln Park Zoo

A stone lion stands tall outside of the Lincoln Park Zoo. 960 1280

  

Al's Italian Beef Sandwich

Al's Italian Beef Sandwich

A must-try when visiting Chicago, Al's Italian beef sandwich lays out on display. 960 1280

  

Chicago's Navy Pier

Chicago's Navy Pier

Bert and the adventurers ride the Ferris wheel at Chicago's Navy Pier. 960 1280

  

Windy City Rollers

Windy City Rollers

Mike poses with the Windy City Rollers after getting his butt kicked on the track. 960 1280

  

Dave and Mike

Dave and Mike

Dave and Mike try out their best gangster poses while enjoying their time at the Gangster Museum. 960 1280

  

Chicago Skyline

Chicago Skyline

Bert, Mike and Dave pose in front of the Chicago skyline after a successful Trip Flip. 960 1280

  

Chicago Pictures  11 Photos

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