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Hideout A ramshackle, roadside house of country-rock in an industrial stretch of town wouldn’t be complete without a few characters hanging out on the porch come summertime. Longtime local acts like Kelly Hogan and Devil in a Woodpile play inside, but the music can still be heard over the cracking of PBR cans out front. 1354 W Wabansia Ave between Willow and Ada Sts (773-227-4433). Bus: 72 North, 73 Armitage. Tue 7pm–2am; Wed–Fri 4pm–2am; Sat 7pm–3am; Sun, Mon (open select days 7pm–2am). Average beer: $2.
June’s Inn Quintessential Chicago, this narrow 30-year-old storefront is a perfect pit stop on the other type of pub crawl. You know, the one where you just want cheap liquor ($2.50 bottles of beer), cool jukebox tunes (the bartender will happily match you dollar for dollar) and a relaxing place to rest your weary head (try a picnic table on the outdoor patio). 4333 N Western Ave between Pensacola and Montrose Aves (773-463-3122). El: Brown to Western. Bus: 49 (24hrs), X49, 78. Mon–Sat 10am–2am; Sun 11am–2am. Average beer: $2.50.
Montrose Saloon This ideal neighborhood dive is somehow still an overlooked gem. The wood paneling is balanced out by exposed brick, a fantastic tin ceiling and stained-glass lamps hanging over the bar. The giant outdoor patio is one of this area’s best-kept secrets—toss horseshoes, play the beanbag game, or just drink and smoke. And don’t mind the new condo-dwellers across the street complaining about the noise; they’ll either move soon or come down to join you. 2933 W Montrose Ave at Richmond St (773-463-7663). Bus: 78 Montrose. Mon–Thu 2pm–2am; Fri, Sun noon–2am; Sat noon–3am. Average beer: $3.
Phyllis’s Musical Inn One of Wicker Park’s first spots for live music refuses to go the way of cover bands by booking local acts that play original rock. They’re not always great, but the garden patio is. A scrappy mix of chairs and tables, a basketball hoop and groups of friends shooting the shit over cheap drinks makes for a classic summer night. 1800 W Division St at Wood St (773-486-9862). El: Blue to Division. Bus: 9, 50, 70. Mon–Fri 3pm–2am; Sat 3pm–3am; Sun 2pm–2am. Average beer: $3.