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Gangster Driving Tour

Al Capone's Prohibition-Era stomping grounds
id_262333
Difficulty: Moderate
Length: 30.2 miles
Duration: 1-3 hours

Overview:  Michael Jordan. Mayor Daley. Al Capone. No matter where you go around the world, these are three Chicagoans people most want to know... more »

Tips:  Most of these sites are in or around downtown Chicago. Look for street parking (make sure you pay at the boxes) or pay parking lots.

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Points of Interest

Now the home of Victory Garden Theater, the Biograph Theater is a must-see spot for gangster buffs. In the early 1930s, bank robber John Dillinger took some of the heat off Al Capone when he was named Public Enemy No. 1. Wanted by the FBI for more than two dozen daring Depression-era bank heists and two jail escapes, Dillinger went to Chicago for ... More

2. Red Lion Pub

Just across the street from the Biograph Theater, the Red Lion Pub was a popular place for a nightcap. Among the satisfied customers was Al Capone. The building dates to 1882. Unfortunately, the restaurant was recently closed.
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2446 N. Lincoln
Chicago

3. St. Valentine's Day Massacre site

Looking at this quiet green space, you'll need to use your imagination as to what once stood and happened here. In 1929 this spot was occupied by a dingy garage—an unlikely site for one of Chicago's most infamous crimes.

On the morning of Feb. 14, 1929, North Side kingpin George "Bugs" Moran was supposed to have an appointment at the... More

Holy Name Cathedral gets a lot of attention because the bullet holes from a famous gangster shoot-out are still gaping in the walls (look for them in the cornerstone). The target of the shooting, Earl "Hymie" Weiss, was rumored to be on his way to meet fellow North Side gang members to discuss how to avenge the death of boss Dean "... More

5. Lexington Hotel

Imagine it's the Roaring '20s and you are the most powerful man in Chicago. Where would you live? In one of the city's most glamorous hotels, of course. As a family man, Capone lived with his wife, Mae, and son, Albert (known as Sonny), in a cozy house on south Prairie Avenue where he cooked Sunday dinners and entertained the family. But most of... More

6. Colosimo's Restaurant

When Al Capone arrived in Chicago, Big Jim Colosimo ruled the South Side. He signed Al on, sending him down the street to the Four Deuces (2222 S. Wabash), where Al used his considerable charm to lure customers in for a drink. He'd then "encourage" them to stay for gambling and other activities. The center of Colosimo's operations was... More

Union Station is the rail hub for Amtrak and Metra trains, always a busy and bustling place. What better place for Eliot Ness to become a hero for saving a baby bumping down the station steps out of control? Of course, that famous scene—straight out of "The Untouchable" starring Kevin Costner as Ness—was totally Hollywood fiction. No... More

8. Sieben Brewery

Back in January 1920 the 18th Amendment enacted Prohibition, which made it illegal to sell alcohol. But that didn't stop thirsty customers from buying it. Nefarious entrepreneurs went into business importing "hooch" (illegal alcohol) from Canada, making "private label" bootleg whiskey and bathtub gin, running lucrative... More

A Roaring '20s-style dinner theater with a speakeasy atmosphere, Tommy Gun's Garage serves up dinner, drinks and a floor show that will transport you back in time. The interactive musical comedy revue features "da gangsters and da flappers and YOU." Singing hit songs from the 1920s, dancing the Charleston, tossing off one-liners that... More

Mount Carmel Catholic Cemetery is the final—if not the first—resting place of the most notorious of Chicago gangsters, Al Capone. Located just outside Chicago in west suburban Hillside off Interstate 290, the cemetery is also the burial place for Capone's brother, Ralph "Bottles" Capone, Jake Lingle, the Chicago Tribune crimer reporter... More

11. Restaurante Klas

Opened in 1922, Klas is the largest Czech restaurant in the United States, known for its Old World decor (amazing), generous portions of home-cooked food and its link to Al Capone. Capone had headquarters in Cicero, and when he was out that way, he frequented Klas, enjoying a hearty meal and, no doubt, a cool Czech beer. According to accounts,... More

Al Capone was a fan of good entertainment and a safe place to hide out. The Green Mill, a jazz club, offered both. Capone had a favorite booth where he could meet with his crew and still keep an eye on the doors.

The club still operates, offering terrific live jazz as well as the popular Uptown Poetry Slam.

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4802 W. Broadway
Chicago
773... More