The Green Mill
No bar in Chicago carries more history per square foot, and the Green Mill earns its rank because the jazz is still genuinely good.
The Green Mill opened in 1907 and reached its apex during Prohibition, when Jack McGurn — Capone’s enforcer — ran the room and bootleg liquor moved through tunnels beneath the floor. The booth Capone favored is still there, still occupied on busy nights by people who know exactly what they’re sitting in. Dave Jemilo rescued the place from neglect in 1986 and restored it meticulously; the tin ceiling, the curved mahogany bar, and the stage are essentially unchanged.
Order whatever you want — there’s no cocktail menu, just a full bar and a bartender who has probably heard everything. The music starts on time and goes late, and on Sunday nights the long-running Uptown Poetry Slam fills every seat. Come for the room as much as the drink, and stay for the second set.
- An Old Fashioned at Capone’s booth
- Whatever the bartender recommends on draft
- A shot and a beer before the second set
