Calling the Jazz Showcase “legendary” feels like an understatement considering how many greats have played here: Dizzy Gillespie, Art Blakey, and Bill Evans, to name a few. And the walls of this nearly 80-year-old South Loop spot—covered in hundreds of old posters, programs, and photos—do a pretty OK job of reminding you of its history. There’s someone on stage here almost every night, so even on a random Tuesday, you can count on getting a jazz serenade after grabbing a table, a seat at the bar, or a spot on one of the old (and slightly crusty) center couches.