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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See & Do
Untouchable Tours

Untouchable Tours offers a full tour of Chicago’s gangster past. Gangsters gained notoriety on Chicago’s streets during the 1920s and left behind a trail of chaos, terror and brutality.

10429 S Prospect Ave
Chicago, IL 60643

 
See & Do
Victory Gardens Theater - Biograph Theater

The Biograph Theater is the location where notorious mobster John Dillinger was gunned down. The theater is one of the many unique stops on Chicago’s Untouchable Tours.

2433 N Lincoln Ave
Chicago, IL 60614

 
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

 
See & Do
The Windy City Rollers

The Windy City Rollers is Chicago’s premiere all-female flat track derby league. Roller Derby is currently in consideration as an Olympic sport and provides action-packed entertainment for the whole family.

525 S Racine Ave
Chicago, IL 60607

 

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