A cursory internet search on Rossi’s includes a lot of (wimpy) people saying they were once afraid to enter the State Street dive. Sure, it’s not exactly the most inviting storefront, but it’s all charm from the moment you walk in — provided you find dark, old bars with beers in coolers and stickers on the walls charming. A sign with a smiley face above the register reads “Cheer Up, Fuckface,” and it’s hard not to crack a grin at the tough love that is also given by the bartenders, who needle regulars and greet everyone else with some degree of warmth. The drinks are affordable, the tunes recognizable, and the stools squeaky. If you could bottle the feeling that sits between sighing at the end of the workday and gearing up for the night ahead, you’d have Rossi’s.
Address: 412 N. State St.
Year opened: 1974
Drink of choice: A beer and a shot
Clientele: Locals, tourists, and Loop workers
Song you might hear: Any hit from the 1970s to the ’90s that can be easily mumbled during the first drink or shouted by the fifth