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.Go to Episode
The Hyatt Regency Hotel is located in the epicenter of Chicago and has a AAA Four Diamond rating. Conveniently attached to Illinois Center, it is also within minutes of Chicago’s “Magnificent Mile.”
151 East Wacker Dr
Chicago, IL 60601
More Chicago Travel Guides
Follow the Chow Masters to find the most creative, off-the-map hot dogs in Chicago.
Find out where to get some of the best takeout food in Chicago.
Find out where to get some of the best burgers in Chicago!
Other Trip Flip Travel Guides
Bert takes newlyweds Craig and Heather Bacon ...
Trip Flip host Bert Kreischer takes an ...
Bert meets the Gross Family in Pittsburgh, ...
Bert finds Sarah McCord and Levi Bennett on a ...
More Travel Inspirations
Enter daily for a chance to win a grand prize worth over $1.5M, located in Atlanta.
Get the essential Food Network email featuring time saving tips, recipes and how-to videos.
Win over the kids with these easy, time-saving dinners the family will love.