Trip Flip: Chicago Pictures

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

Photos

Seattle

Seattle

Bert and vacationers Will and Kristi conquer white water rapids in Seattle. 960 1280

  

Seattle

Seattle

Bert, Will and Kristi get lessons in extreme hula hooping. 960 1280

  

Seattle

Seattle

Bert, Will and Kristi learn the finer points of foraging by a creek from author Langdon Cook. 960 1280

  

Denver

Denver

Rocky Mountain vacationers, Paul and Jennifer, prepare to paraglide around Denver. 960 1280

  

Denver

Denver

Bert and the Rocky Mountain vacationers take a quick break from biking to take in the view. 960 1280

  

Denver

Denver

Paul and Jennifer hop on a couple of trusty steeds and hit the rocky trail. 960 1280

  

Sydney

Sydney

Bert and Sydney vacationers Tom and Robyn learn the ways of the Aborigines. 960 1280

  

Sydney

Sydney

Tom and Robyn get a crash course in lifeguarding Down Under. 960 1280

  

Sydney

Sydney

Does this look like the face of someone who just found out they'll be taking a helicopter tour over Sydney? 960 1280

  

Great Barrier Reef

Great Barrier Reef

Bert and vacationers Katie and Ryan learn the rules to fooket, a combination of football (rugby) and cricket -- 2 of Australia's most popular sports. 960 1280

  

Great Barrier Reef

Great Barrier Reef

Bert and the vacationers get ready to ride a trail in Queensland. 960 1280

  

Las Vegas

Las Vegas

Bert and his Vegas vacationers, Kim and Kyle, find themselves surrounded by 360 degrees of fun. 960 1280

  

Las Vegas

Las Vegas

What happens in Vegas, hopefully won't stay in Vegas … this time! Kim said she would, and Kyle did. 960 1280

  

Los Angeles

Los Angeles

Bert finds himself in yet another sticky situation with Los Angeles vacationers Jamian and Ventana. 960 1280

  

Los Angeles

Los Angeles

Bert, Jamian and Ventana prepare to paddle board in the Pacific. 960 1280

  

Austin

Austin

Bert introduces Austin vacationers Rebecca and Maxim to the Courtyard Hounds. 960 1280

  

Austin

Austin

Maxim takes a few minutes to regain his bearings after Bert convinces him to go bull riding. 960 1280

  

Chicago

Chicago

We have liftoff! Bert takes off on a jet surfing session while vacationing in Chicago. 960 1280

  

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