On the season finale of Trip Flip, Bret surprises Californians David and Mike with the ultimate, all-expenses-paid dream vacation to the Windy City of Chicago.

In this amazing, tailor-made guys’ getaway, David and Mike see a side of Chicago that most people will never have the opportunity to experience. Bert kicks the trip off with an introduction to the latest craze in water sports: Flyboarding on Lake Michigan. After propelling themselves 20 feet into the air using high-powered water jet streams, it’s on to the edgier side of Chicago to see the gangster hotspots of the ‘20s and ‘30s on a mobster tour. And that’s just the first part of day 1!

To find out what other exciting adventures David and Mike were lucky enough to experience, tune in for an all-new episode, tonight at 8|7c.

Plus, don’t miss these exclusive, behind-the-scenes photos from our Chicago Trip Flip.

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Ben BreslermanBorn and raised in Potomac, MD, Ben now resides in Washington, DC, after graduating from Arizona State University. Before becoming an Interactive Producer for TravelChannel.com, Ben was a web producer...

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