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.

Go to Episode
Filter: See & Do
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

 

More Chicago Travel Guides

Chow Masters: Chicago Travel Guide

Follow the Chow Masters to find the most creative, off-the-map hot dogs in Chicago.

Best Daym Takeout: Chicago Travel Guide

Find out where to get some of the best takeout food in Chicago.

Burger Land: Chicago Travel Guide

Find out where to get some of the best burgers in Chicago!

More Travel Inspirations

HGTV Urban Oasis
HGTV Urban Oasis 2014

Enter daily for a chance to win a grand prize worth over $1.5M, located in Atlanta.

Food.com App
Download the New Food.com

Get recipe inspiration, save money on groceries, and plan your meals stress free.

Food Network Back to School
Food Network's Back to School Recipes

Win over the kids with these easy, time-saving dinners the family will love.