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
Al’s is a Chicago must-have. The Italian beef sandwich is Chicago’s answer to the Philly Cheesesteak. The beef is marinated and slow-cooked for 8 hours before being thinly sliced and placed on an Italian-style roll with hot and sweet peppers.
1079 W Taylor St
Chicago, IL 60607-4224
Archie’s is the perfect introduction into Chicago’s famous neighborhood dive bar scene. This bar is a local favorite, loved for its awesome staff, drink specials and bar food.
2600 W. Iowa St
Chicago, IL 60622
Notorious Chicago gangster Hymie Weiss was gunned down on the steps of this iconic gothic-style cathedral in Chicago.
730 N. State St
Chicago, IL 60611
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
Flyboarding is the latest and greatest in water sports Learn what it’s like to fly by strapping on a water-propelled jet pack -- attached to a jet ski -- and using hand-operated controls to soar above the water.
Klas Restaurant was the hangout for notorious Chicago gangster Al Capone. Klas opened its doors in 1922 and today is considered one of the few remaining restaurants in Chicago serving Eastern European food.
5734 W Cermak Rd
Cicero, IL 60804
O’Hare International Airport has been ranked as the best airport in North America for 13 consecutive years by the Global Travel Awards.
10000 West O’Hare Ave
Chicago, IL 60666
Located on Navy Pier, the Red Witch is Chicago’s tallest -- and only -- wooden ship. If Chicago is the Windy City, why not put some of that wind to use? A ride on the Red Witch is an authentic sailing experience.
800 E Waldron Ave Dock J
Chicago, IL 60605
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
Buckle up and take a tour of the most thrilling amusement parks in America.
Try Food.com's quick and easy apps for a stress free turkey day.
Plan Your Menu with easy, how-to videos from Bobby, Sunny and more.