Green Mill Cocktail Lounge
One of Chicago’s oldest bars, this 1907 original served as notorious gangster Al Capone’s favorite Prohibition-era hangout. These days, Green Mill remains one of the top jazz clubs in the country as well as a damn fine spot to grab a drink. The cinematic vibes of this bucket list-worthy bar are impossible to miss (with several film scenes being shot here), especially when bands hit the old-timey stage. It’s also a top post-show spot after catching a concert at the nearby Riviera or Aragon. Drinks are nothing too fancy or gimmicky, just strong and delicious. Just don’t chat too loud while the bands are playing or you will be unceremoniously shushed.
How to book: Stop by for first come, first served seating.