Chicago, IL, Travel Guide

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.

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Al's Italian Beef

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

 
Eat
Archie’s Iowa and Rockwell Tavern

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

 
Eat
Klas Restaurant

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

 
Eat
The Weiner’s Circle

The Weiner’s Circle is one of the most famous hot dog restaurants in the country. But beware: a late-night visit may result in the staff serving up a little Chicago-style attitude with your hot dog.

2622 N Clark St
Chicago, IL 60614

 

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