The venerable Ukrainian Village dive has been the pinnacle of cool since ’92, when it opened in a self-described “cat-ridden hole-in-the-wall.” With its worn couches and cracked linoleum, it still looks like it’s seen some things—including legendarily rowdy shows from bands just before they hit the big time. (In 2001, a fledgling band called The Strokes opened for Guided by Voices in a performance that involved a stripper and ended in a guitarist passing out from too much whiskey.)

Owner Joe Shanahan opened the city’s preeminent alternative venue (and its downstairs sister club, Smartbar) in 1982 as Chicago’s answer to culture-shifting ’70s NYC spots like CBGB. In the 40 years since, Metro’s built a reputation as not just a gorgeous century-old concert space, but a tastemaker: They booked R.E.M. for the grand opening, championed The Smashing Pumpkins before they got big, and served as a springboard for pop-punk legends Fall Out Boy and a teenage Chance the Rapper.

A historic landmark in the culturally rich Pilsen area, the gorgeous Romanesque venue was built at the turn of the 20th century as a luxe theater and meeting place. Restored to its original grandeur and relaunched as Thalia Hall in 2013, the multiuse space plays a similar role in the community, with a vibey punch bar and restaurant beneath the ornate 800-capacity concert hall, which hosts a discerning range of rock, rap, and electronic shows—from Cat Power to sunn O))) to Shygirl.

The historic Uptown auditorium is an architectural gem; at the time of its opening in 1926, it was called the most beautiful ballroom in the world, designed in the style of a Spanish palace courtyard with crystal chandeliers, Baroque balconies, and mosaic tiles. Known in the ’70s as the Aragon Brawlroom for its notoriously wild rock concerts, the 5000-capacity space now hosts extravagant EDM shows, rising bands like Turnstile, and big-name rappers like Tyler, the Creator.

The Lakeview tavern is one of 10 buildings that remain of the 57 erected by the Schlitz Brewing Company in Chicago at the turn of the 20th century, complete with the signature Schlitz globe on the brick exterior. Restored and opened as Schubas in 1989, it’s among the best small venues in the city. The front room’s a friendly neighborhood pub; the back room’s a 165-capacity space for electronic acts like Disclosure or cutting-edge rappers like Armand Hammer.

Since 2007, the South Loop club has been a hub for all kinds of scrappy, unorthodox sounds, from esoteric SoundCloud rap to Swedish death metal to screeching street punk. Once a dingy auto repair shop, the multilevel space boasts multiple stages (one in the exposed-brick bar-and-grill area, another in the larger Reggies Rock Club), plus a rooftop deck and a handy fleet of vintage buses to cart those in need of a designated driver to nearby venues.

Opened in 2009 by the team behind Schubas, the 500-capacity Lincoln Park venue has its finger on the pulse of new music. Originally built in 1912, the former Fullerton Theater now books rappers you can impress your friends by being up on (BabyTron, RXKNephew), pop futurists (Caroline Polachek, Charli XCX), plus the occasional tasteful legacy act like The Dream Syndicate. Along with Schubas, it’s home to the forward-thinking five-day Tomorrow Never Knows festival every January.

The decidedly un-touristy rock bar is tucked under the El tracks a block away from Union Park (where Pitchfork Music Festival is held every summer), identifiable by the red glow of its vaguely sinister serpent sign. A compact brick space filled with skull and Harley-Davidson paraphernalia, it’s a lesser-known hub for punk, metal, and straight-up rock ’n’ roll, plus juicy burgers and a solid tap list.

Initially built in 1917 as an ornate movie theater, the Riv long operated as a nightclub before changing gears in the late ’80s, when it became one of Chicago’s most popular music venues. (It’s just down the street from the similarly majestic Aragon Ballroom.) Since then, its lavishly detailed stage has been the setting for Pantera music videos, Smashing Pumpkins release parties, and Tame Impala live albums; today you might catch Wilco, Weyes Blood, or Yves Tumor performing here.

The city’s newest large-scale venue is actually a nearly century-old landmark: the Morton Salt Company warehouse complex, whose massive rooftop logo beckoned from an industrial but scenic corridor along the Chicago River. In 2022, The Salt Shed reopened the shuttered site as an impressive indoor-outdoor concert venue where you can catch the likes of Iggy Pop, The Roots, or Tove Lo, with the panoramic Chicago skyline as a backdrop.