Relive the Roarin' Twenties in Al Capone Style in Chicago Today

Massacres, trap doors and Chicago jazz. It’s the way Al Capone and his Chicago Outfit experienced Chicago in the 1920s. The rich, bloody mark that Chicago’s mob bosses left on the streets is still — sometimes begrudgingly — remembered by many. Recently, we took a trip to Chicago to discover where the old speakeasies used to be and where the St. Valentines Day Massacre occurred, grabbing a pizza along the way.

Room 21

Don’t be fooled by the ornate designs, this restaurant has a dirty history. At the peak of Capone’s business, this was his largest speakeasy and brewery in all of Chicago.

At first glance, Room 21 is simply an upscale American restaurant with a large bar and a wide-open patio. In one corner, however, lies one of Capone’s best-kept secrets. “There was the original foundation here,” Manager John Nowowiejski said, motioning to the corner at the end of the bar. “But when we were doing some work putting the plumbing in for the cappuccino maker, we found something. So Jerry Kleiner, the owner said ‘tear it all down’ and we found this passageway.”

The passageway, now lit with an incandescent red glow, narrowly follows the edge of the building. You can see the original brick on either side, claustrophobically coercing you up the stairs. And under the newly added stairs, the top corner of a door peeks out. Leading to the street, the door was probably one of Capone’s exits.

Another door existed at the top of the stairs. “At the end of the passageway, we found a door with the number 21 hanging on it,” Nowowiejski said. “And that’s how we got the name of the restaurant.”

“We actually don’t know much of what happened here,” Nowowiejski said, opening the door at the end of the hall. The inside has been radically changed to a room with classical artwork and a table overlooking the kitchen. “The unknown about it adds to the mystique.”

Not only did Room 21 house Capone’s largest brewery, it was one of his largest busts. Eliot Ness of the Untouchables, the Chicago police group designed to deal with the mafia, led his team into the speakeasy with a 10-ton truck and seized two hundred thousand gallons of alcohol.

Getting there: Take the red line to Cermak/Chinatown and turn left until you get to South Wabash. 2110 S. Wabash St.

Green Mill Cocktail Lounge

To see one of Al Capone’s favorite clubs, head over to the Green Mill Cocktail Lounge. His booth is the first one you see walking past the old jazz posters and decorative walls. And don’t expect a menu; everything served here comes in a glass, not on a plate.

“Al Capone was also a regular here,” owner Dave Jemilo said. “He would sit in a booth by the wall so he could see both doors. That’s what you do. There was a way people could come from behind and get him, but he had guards to check his back.”

And if Capone ever needed a quick escape route, he had his own way out. “There was a trap door for him behind the bar where he could escape if need be,” Jemilo said. “There was a series of tunnels and passageways that would lead outside. I’m the only one with the key, and I wouldn’t let you down there anyway.”

Jack “Machine Gun” McGurn, one of the men responsible for the St. Valentine’s Day Massacre, was a part owner of the club at one point. And when the headlining singer left for a rival club, McGurn took action himself.

“His favorite singer at the club was Joe E. Lewis, but Lewis was offered a better deal at Rendezvous Club,” Jemilo said. “McGurn told Lewis that he signed a deal for life at Green Mill, but Lewis quit anyways. So a week later, McGurn went to Lewis’s hotel and cut off his tongue and slit his vocal cords so he could never sing again. He almost died, but he eventually came back as a comedian and became a famous comic.”

Frank Sinatra later immortalized Joe E. Lewis in The Joker Is Wild, a movie detailing the whole fiasco.

Getting there: Located off the Lawrence stop on the Red Line in Uptown, the Green Mill Cocktail Lounge is the perfect place for a drink before or after a show at the Aragon. 4802 N. Broadway Ave.

Chicago Pizza and Oven Grinder Co.

The St. Valentine’s Day Massacre of 1929 was the turning point for the infamous Chicago Outfit. While Capone was enjoying a vacation in Florida, part of his south-side gang, two dressed up as police officers, allegedly lined up four of Bugs Moran’s north-side gang inside a garage. With Moran’s gang against the wall, Capone’s henchmen opened fire. Jack “Machine Gun” McGurn, part owner of the Green Mill Cocktail Lounge, was the purported leader of the shooting.

Across the street on the second floor of what was a boarding house, two other members of Capone’s gang kept watch. And today, on the first floor, is Chicago Pizza and Oven Grinder Co., a unique and original restaurant located in the middle of Lincoln Park.

You can still see where the massacre took place, but there is no garage left. “Mayor Daley tore down the garage and now it’s an empty lot,” Manager Cathy Gallanis said. “No plaque or anything about it. He didn’t want a reminder of what happened.”

As for the pizza here, it isn’t what you would normally expect, Gallanis said. It’s called pizza pot pie. “We take a ceramic bowl layered with our homemade dough and then add a layer of cheese. Then we ladle in our homemade sauce, with or without sausage, and throw in whole, fresh mushrooms. We put some white or wheat dough on top and cook it. Then at the table, we flip it over and that’s it.”

Recently featured on Rachael Ray, Chicago Pizza and Oven Grinder Co. will continue to serve its unusual cooking. “In a world of franchises, we try to be unique and original,” Gallanis said. “We’ve had the same menu since we opened in 1978.”

Getting there: Get off at the Armitage stop on the brown line and head east on Armitage Street then north on Clark Street to pay homage to one of the most violent events of the 1920s, and one of the most forgotten places too. 2121 N. Clark St.

Tommy Gun’s Garage

To literally relive the Prohibition era (the drinking side of it, not the dry), head south to Tommy Gun’s Garage. Owners Kris Adams and Sandy Mangen emulate the original speakeasies to a tee, not leaving out any details.

“We’re running an illegal speakeasy here,” Adams said. “There are no signs out front, and we have a doorman to check everyone who comes in. He wears gloves so he won’t leave any fingerprints and he will only let you in if you say the password.”

The servers are not just servers, but gangsters with holsters or flappers with dresses. After dinner, the entertainment begins. “The show is basically a musical comedy review, “ Adams said. “We have the sing and dance numbers in the beginning and after that we have vaudeville skits with an Abbott and Costello type act. The show has a lot of audience involvement. At one point, the cops show up and bust everybody there.”

Getting there: Get off the El at Cermak/Chinatown on the Red line and turn left. Reservations are required, so call (312) 225-0273, and don’t forget the password. 2114 S. Wabash Rd.

For its tame Midwestern reputation, Chicago has a rich and violent history riddled with secrets and hidden tunnels. Next time you go downtown, add interest to your usual destinations by making a night of a mafia hangout. Your historical knowledge will impress your friends, your date, or your parents alike — and chilling where Capone chilled? Badass.

Thanks to Alex Freeman