The Green Mill

"Famous for being Al Capone's former stomping grounds — complete with legendary subterranean pathways where the infamous mob boss used to run booze — the Green Mill in Uptown is a classic tavern for music and a stiff drink. They don’t make bars like this anymore with a rich interior that echoes the venue’s past. The bar has opened up its window, allowing patrons to sit on the sidewalk for outdoor seating." - Ashok Selvam, Naomi Waxman

"Charlie Chaplin, Frank Sinatra, and Al Capone are just a few of the big names who have hung out at this classic jazz club over the 100 years it’s been open. Translation—The Green Mill has seen some sh*t, and it’s still one of the best places to catch live jazz music every day of the week. Rumor has it there’s a crazy set of underground tunnels beneath the place where your wildest gangster dreams took place, which is fun to think about even if they won’t give you a tour." - josh barnett, sam faye, john ringor

"This cash-only, cocktail lounge used to be one of Al Capone’s favorite Uptown spots, complete with secret booze-smuggling tunnels. Unfortunately, those are no longer in commission (so you can’t use them to dodge the cover fee), but this venue still maintains the old-timey decor, and has a fantastic regular line-up of jazz music. Come here to sit at their large wooden bar and sip on a strong Old Fashioned, or to drink stiff martinis in a big booth while a big band blasts Duke Ellington. " - john ringor, nick allen

"A landmark that's been witness to Al Capone and more. No trip to Chicago would be complete without a martini at this jazz Mecca. The bar is about the music not conversation. Please abide by the house rules." - Ashok Selvam, Naomi Waxman

"You can pop in for a drink at The Green Mill, a watering hole beloved by gangster Al Capone."