The Green Mill Cocktail Lounge is among the city’s iconic jazz clubs, and unquestionably the most persistent: You can catch live music every night of the week without fail. There’s a consistent rotation of expert players and ensembles zipping through primarily swing, bop, and modal jazz, but the main draw is the Mill itself, because nothing like it exists anymore. Opened in 1914, the edifice is one of the last vestiges of Prohibition-era Chicago, a space packed with details and filigrees long expired from collective memory: an impossibly long hook-shaped bar, with a small stage behind its crux; fresco paintings on the walls surrounded by cartoonish frames; candlelit booths with crushed velvet seats the color of pea-green soup. The Green Mill even gained notoriety as a joint where Al Capone reportedly used to hang out (and was said to elude authorities through underground tunnels connecting the bar to the building next door). Prepandemic it was also the city’s greatest late-night bar, with a 4 a.m. license grandfathered in (and impossible to come by nowadays). The price is anywhere from $10 to $30 at the door, depending on the act, but it’s free after midnight (and for the time being, the club is open until 2 a.m. on weekends). So you can still drink pretty late, and it’s the one place you won’t regret doing that the next day. 4802 N. Broadway, Uptown