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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Eat
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

 
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

 
Sleep
Hyatt Regency

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

 
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.

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

 
Travel
O’Hare International Airport

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

 
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

 

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