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.


Activities
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.

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.
Chicago, IL, US
Phone: +1 312-399-9852
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 North Lincoln Avenue
  • Chicago, IL 60614 US

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 North Lincoln Avenue Chicago, IL, US
Holy Name Cathedral
Notorious Chicago gangster Hymie Weiss was gunned down on the steps of this iconic gothic-style cathedral in Chicago.
  • 730 North State Street
  • Chicago, IL 60654 US

Holy Name Cathedral

Notorious Chicago gangster Hymie Weiss was gunned down on the steps of this iconic gothic-style cathedral in Chicago.
730 North State Street Chicago, IL, US
Phone: +1 312-787-1544
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.
  • 600 North clark St
  • Chicago, IL 60643 US

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.
600 North clark St Chicago, IL, US
Phone: +1 773-881-1195
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.
  • 600 E Waldron Dr
  • Dock J
  • Chicago, IL 60605 US

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.
600 E Waldron Dr Chicago, IL, US
Phone: +1 312-469-0233
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 South Racine Avenue
  • Chicago, IL 60607 US

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 South Racine Avenue Chicago, IL, US

Hotels
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 Upper Wacker Drive
  • Chicago, IL 60601 US

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 Upper Wacker Drive Chicago, IL, US
Phone: +1 312-565-1234

Restaurants & Bars
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 West Cermak Road
  • Cicero, IL 60804 US

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 West Cermak Road Cicero, IL, US
Phone: +1 708-652-0795
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 West Taylor St
  • Chicago, IL 60607 US

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 West Taylor St Chicago, IL, US
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.

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.
Chicago, IL, US
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 West Iowa Street
  • Chicago, IL 60622 US

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 West Iowa Street Chicago, IL, US
Phone: +1 773-486-2626

Transportation
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.

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.
Chicago, IL, US

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