Culture + Style

Walk Where Chicago’s Most Notorious Gangsters Walked

Green Mill Cocktail Lounge, frequented by Al Capone (Photo: Ten Photos)

These days when you hear Chicago you think the Obamas, Oprah, Derrick Rose, Stephanie Izard and Rahm Emanuel. But there was a time when Chicago was known for its notorious mobsters like Al Capone and Bugs Moran. These gangsters had hangouts — private clubs, brothels, music halls — where they’d gather their cronies, drink whiskey and launder money. Some of the buildings still stand while others have been razed and replaced with newer buildings or a parking lot. So much for history right? Fortunately some of the places still exist. Shall we take a look?

Al Capone and the Green Mill

Al Capone is likely Chicago’s most notorious gangster and if you watched “Boardwalk Empire,” you glimpsed his fierce temper. Since he had enemies everywhere, numerous escape tunnels and hidden rooms were constructed at his one-time headquarters at the Lexington Hotel on Michigan Avenue at 22nd Street.

But the best place to get a feel for Capone is at The Green Mill Cocktail Lounge. Capone hung out at this jumpin’ jazz club in the Uptown neighborhood where greats like Tommy Dorsey and Billie Holiday performed. Whenever Capone would enter, the bandleader reportedly stopped playing whatever song to begin Capone’s favorite, “Rhapsody in Blue.”

The gangster sat in a booth near a side exit where he could see anyone coming or going. There was a trap door behind the bar that had an elevator leading to hidden tunnels to numerous buildings in the area. The Green Mill has operated since the early 20th century and still attracts jazz lovers from all over the world.

John Dillinger and the Biograph Theater

John Dillinger, a.k.a. Public Enemy No. 1, was one of the country’s most notorious bank robbers during the Great Depression, knocking off about a dozen banks to the tune of around $500,000 (about $7 million today). His good looks and smooth talking also made him a fan of the ladies, which would ultimately prove to be his downfall.

In the summer of 1934, Dillinger holed up in a Chicago apartment with two women, Polly Hamilton, and brothel owner, Anna Sage, and would often check out Chicago Cubs games at Wrigley Field.

When Dillinger’s bounty rose to $25,000, Sage, who would come to be known as the “woman in red,” worked out a deal with the FBI so she wouldn’t be deported back to Romania. On July 22, 1934, the trio attended a screening of gangster movie “Manhattan Melodrama” starring Clark Gable at the Biograph Theater at 2433 N. Lincoln in Lincoln Park.

When they emerged from the theater, Dillinger was gunned down by a group of Feds who were there to arrest him.

The theater, now on the National Register of Historic Places, was turned into a live performance venue and is now called the Victory Gardens Biograph Theater.

Big Jim Colosimo and Colosimo’s Café

As a big time gangster, why not have your own club? That’s exactly what James “Big Jim” Colosimo did when he opened Colosimo’s Café at 2126 S. Wabash in Chicago’s infamous Levee District. The notorious gangster opened the club in 1909, first as a more modest cafe, but it would eventually turn into a nightclub with showgirls and a large orchestra.

At one time, you could get a full frog leg dinner for $1.25 or chicken dinner for $1.50 while you watched a cabaret. Silverware even graced a special Colosimo’s stamp.

While the restaurant would continue to operate into the 1950s, Big Jim himself was gunned down at the site, reportedly by a hired gun of Al Capone and his then-boss, Johnny Torrio, in 1920.

Speaking of Torrio, he built out an infamous brothel at 2222 S. Wabash, just down the street from Colosimo’s. While both of the buildings have been demolished, there is plenty to do in the area, the South Loop. Take in a rock show at Reggie’s (2105 S. State) or dance to hip-hop or house music at The Shrine (2109 S. Wabash).

Hungry? Try the Michelin-starred Acadia (1639 S. Wabash), where you can get one of the best burgers or lobster rolls at their bar if you’re not in the mood for their pricier tasting menu.

Dion “Dean” O’Banion at The Drifter

One of Chicago’s newest bars is actually one of its oldest: The Drifter. This former speakeasy set beneath The Green Door Tavern, which opened in 1921 as an Italian restaurant and grocery, was a main hangout for Dion “Dean” O’Banion and his North Side Gang, which also included Hymie Weiss, Vincent Drucci and George “Bugs” Moran.

Chicago’s notorious “Beer Wars” didn’t begin until 1923 and prior to this, it’s reported that O’Banion had close ties with South Side gangsters Johnny Torrio and Al Capone, who also allegedly spent time hanging out at the speakeasy, according to Jonathan Knotek, who runs Chicago Prohibition Tours.

These days, the space operates as The Drifter, which opened January 2015. Much of the space looks just as it did back in the 1920s: Many of the wine and liquor bottles, tapestries, signs and other knick knacks found when the speakeasy opened were cleaned up and still sit on the walls and shelves. T

he bar is now open Wednesday through Saturday nights, is accessible behind a hidden door in the Green Door’s basement and charges a nominal cover fee for nightly entertainment, which often features burlesque performances, musical acts and magic shows.