2421 N Milwaukee Ave
Chicago, IL 60647
The cool kids gather in this tiny, intimate Logan Square bar chiefly known for its top-notch mixologists and rotating menu of seasonal cocktails. The Whistler books live music and DJs throughout the week, with many of the acts represented on the bar’s in-house label Whistler Records. The live bands run the gamut from local underground indie rock to free jazz, world and electronica. Because there’s never a cover, the line grows out the door pretty quickly.
The Red Line Tap
7000 N Glenwood Ave
60626-2803 (773) 274-5463
The Rogers Park joint formerly—and perhaps more famously—known as “Roy’s” received a revamp and a new name when it’s original owner, Roy Kawaguch, passed away in 1996. Now known as The Red Line Tap, this friendly neighborhood bar and sister establishment to the Heartland Cafe is home to a weekly open mic night, and brings in a range of genres throughout the week. Though the taproom books plenty of alternative, singer-songwriter and roots style music, it has become especially well-regarded for Heavy Metal and hard rock.
1530 N Milwaukee Ave
Chicago, IL 60622 (773) 276-7036
Video installations and viewings tend to dominate this Wicker Park mainstay, though Rodan books ultra-hip bands whenever the projector’s not running. Rodan frequently features artists from Chicago-based independent labels, like Addenda Records and Thrill Jockey, making it a prime spot to catch bands in their pre-buzz period. For those who love consistency, Rodan also keeps a steady Monday night residency for experimental and avant jazz.
Honky Tonk BBQ
1213 W 18th St
Honky Tonk BBQ isn’t just home to some of the finest brisket in the city, it’s also the go-to spot for Southern-style music. The floor in front of the BBQ joint’s “Saloon Stage” is where the diners become dancers, showing off their moves to the music of whichever Americana, Western Swing, Honky Tonk, Rockabilly, Bluegrass, Blues, Old Time and Soul act is booked that evening. The Pilsen-based restaurant gets especially lively after dinner, once most folks have finished their BBQ and are a few drinks in. Don’t be intimidated by the regulars on the dance floor – most are happy to teach a few moves to the newbies.
The Green Mill
4802 N Broadway St
Chicago, IL 60640
This venerable Uptown lounge is famous as a former Capone hangout and as a Chicago jazz institution. Classy but comfortable, old-timers and fresh faces alike mingle over cocktails to hear jazz varieties that stretch from New Orleans style to Dixieland to Bebop. The Green Mill is especially good for the second-shifters and other night owls: even though many of the performers are well into their 70s and 80s, it’s pretty common for jams to go on until sunrise.