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

Getting There

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

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