WATCH: See the Secret Tunnels in Al Capone’s Favorite Chicago Bar

The Green Mill, in Chicago’s uptown neighborhood, is more than just a great jazz bar. It also has a lot of history. Back in the 1920’s, the bar was the favorite hangout of none other than legendary gangster Al Capone. Capone’s buddy “Machine Gun” Jack McGurn owned the place, and Capone even had a favorite booth where I got to sit and drink.

Capone’s favorite booth has good views of all entrances and exits — perfect for a gangster — but Capone himself didn’t always go out the front door. Behind the bar is a trap door down to the basement, where tunnels lead to alternate exits in other buildings. That way, says Green Mill owner Dave Jemilo, he was far away by the time anyone, including the police, could find him. “Say they’re looking for Capone [and] say, ‘Hey, weren’t you in the Green Mill?’ He says, ‘No, I’m walking with my girl. I’m coming from the movie show, leave me alone.’”

The exterior of Green Mills (Photo: Melanie Dunea)

Jemilo says Capone was a great customer to have around, buying everyone drinks and tipping the staff a hundred dollars each.

These days, the bar is a much milder place, but the drinks are still old-school. (Looking for more great cocktails in Chicago? Check out these bars. I took a taste of Jeppson’s Malort, a liquor that’s a Chicago original. It’s made with the root of the wormwood plant. I can’t say I enjoyed it. The aftertaste reminded me a bit of earwax! Luckily, the bar carries another Chicago original, Schlitz beer, to wash it down.

Bottom’s up at Green Mills (Photo: Melanie Dunea)

What: The Green Mill

Why Go: To step back in time to the days of Al Capone and gangsters … and to have a shot of Malort.

Where: 4802 North Broadway Street in Chicago’s Uptown neighborhood

Fun Fact: Rumors have it that when Capone visited the bar, no one could come in or out while he was there.

Looking for another Prohibition-era establishment bar — and one with food, too? Check out my visit to Cole’s in Los Angeles for a French Dip sandwich and an old fashioned.

Photo Tripping is a Yahoo Travel original series hosted by renowned celebrity photographer Melanie Dunea (author of My Last Supper<. Melanie takes us on a photographic journey with her as she visits America’s top cities to experience the best tastes, sounds, and sights the city has to offer.

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