If there’s one place in Chicago that oozes its quintessential jazzy charm that dangerously flirts with a heavy history of mafia, then the Green Mill Jazz Lounge is your place. Not having changed much since its opening in 1907 (yes, 1907), the place is dark, smoky (even still, post no-smoking laws somehow) and sexy.

Back in the day the place had an outdoor dancing and drinking garden lit by lanterns, where people arrived by horse and buggy. The garden was complete with horse-hitching posts. It soon transpired to be a mobster hangout when some of Al Capone’s henchmen became part owners. So much drama went down here that Sinatra himself played a singer whose throat and  tongue were once slit in this club over good ol’ mobster issues. Alas, Sinatra had to spend some quality time for “research” at the Green Mill as well.

It survived prohibition as a speakeasy and the decor of that era remains. Today, you can catch killer jazz there any night of the week, Mondays being a favorite for the Patricia Barber quartet. It’s all about the music and history here so don’t get too glammed up unless you’re trying to live vicariously through its history by transporting yourself in an immersion of jazz notes, strong cocktails and a big black booth that maybe Capone himself sat in: in which case, you just may be able to pull it off.