A beloved and historically resonant tavern in a city full of them, the Rainbo’s distinctive sign of red neon with a green cocktail-glass detail has lured generations of hipsters to the key Wicker Park intersection of Division and Damen.  

The interior appears unchanged from the 1940s, except for installations from local artists; Liz Phair took the revealing cover picture for her debut Exile in Guyville in the photo booth, and rockers from bands both respected (Tortoise) and infamous (Urge Overkill) may still be found sipping a reasonably priced drink here or occasionally giving word-of-mouth performances.

 Also, many members of Chicago’s tight-knit music community have found work behind the horseshoe-shaped bar (it conceals a small stage from the burlesque era, sadly unused.)  That quiet fellow at the taps who looks like a cool-dad tax accountant is probably Rick Rizzo, scorching guitarist from longtime scene survivors Eleventh Dream Day.  

Enjoy their company, and the impeccably curated all-vinyl soundtrack, but be warned: it’s beyond packed on the weekends.  Come early to score one of the desirable booths, and yes, the Tamale Man will be in later to address any tipsy cravings with a $6 bag of tamales.