Green Mill cocktail lounge

If you are tired of sports bars and want to impress your date with a classic Chicago jazz club, plan your next outing at the Green Mill Cocktail Lounge. Combine live New Orleans-style jazz, 1910s prohibition-style with Chicago’s mob history and you’ve got one of the best dates in Uptown. Its popularity is in part due to its historical appeal; the lounge was a notorious speakeasy owned by “Machine Gun” Jack McGurn, an associate of Al Capone. Capone even had a special booth that allowed him to keep an eye on both entrances while enjoying the show. To Al Capone, this was the best seat in the house. You can see his quote on the wall today and the rumored trap door that he used to sneak out of. Some of the most famous jazz singers have performed here, including Billie Holiday and Tommy Dorsey. Open seven days a week from 4 p.m. to 1:30 a.m., Green Mill is one of the oldest continuously running — up until the pandemic — jazz clubs in the country.

The Green Mill is different from the usual happy camper, no cocktail list, no credit cards and no reservations. This club does not play around but consistently holds an intriguing vibe for a perfect evening.