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.

Travel Guide

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Chicago Pictures

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02:47

The Windy City Rollers

Bert introduces David and Mike to the Chicago women's roller ...

02:36

Swim With Sharks

Two unsuspecting vacationers swim with sharks in Hawaii.

Paddle Boarding

Bert takes 2 vacationers paddle boarding on the waves in Oahu.

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