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
Holy Name Cathedral

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

See & Do
Jet Surf Chicago

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.

See & Do
Red Witch

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

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

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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