Chris’s Northland Tavern
This nondescript neighborhood bar, an unpretentious dive where older guys play pool and shoot the breeze while Aerosmith blasts on the jukebox and the always-irate bartender serves cold beers, seems almost out of place in Wicker Park. Some of the regulars are real characters, such as the guy donning a hat covered in foil-wrapped cigars, and they warm up to you once everyone’s had a few drinks. 1610 W North Ave between Ashland and Marshfield Aves (773-342-8181). El: Blue to Damen. Bus: 9 (24hrs), 50, 72. Sun–Fri 7pm–2am; Sat 7pm–3am. Average beer: $4.
Davenport’s Piano Bar and Cabaret
Wicker Park’s only piano bar has been around since 1998, when most area shoppers and sippers were still in school. Karaoke is a big part of the place: The back room bursts with would-be crooners on Friday nights. And on the other nights? Professionals—replete with boas and dirty jokes—show them how it’s really done. 1383 N Milwaukee Ave between Wolcott Ave and Wood St (773-278-1830). El: Blue to Damen. Bus: 50, 56, 72. Mon, Wed, Thu 7pm–midnight; Fri, Sat 7pm–2am; Sun 7–11pm. Average cocktail: $9.
Ed and Jean’s
It’s not that this old Bucktown standby feels like somebody’s living room; it’s that it basically is one. Jean’s been here for 55 years, and in that time she’s accumulated more knickknacks than a flea market. It’s her second home, and after a few minutes chatting with her over a cheap bottle of beer, it starts feeling like yours, too. 2032 W Armitage Ave between Damen and Hoyne Aves (no phone). El: Blue to Western. Bus: 49 (24hrs), 50, 73. Average beer: $2.50. Cash only.
The Flat Iron
When this place was The Note, the focus was on the bands on stage. Now, of course, those bands are gone, and the focus is on…nothing. The dark bar, now decorated with street-art murals on the walls, is roomy and a little divey, and it’s essentially as low-key and basic as a bar can get. And that’s exactly what this rapidly yuppifying neighborhood needs. 1565 N Milwaukee Ave at Damen Ave (773-365-9000). El: Blue to Damen. Bus: 50, 56, 72. Sun–Fri 4pm–4am; Sat 4pm–5am. Average beer: $4.
Perhaps one of the most active and random stages in the city can be found at this eclectic, art-filled corner tavern, where nightly performances can range from poetry readings to jam bands to a recent musical tribute to a famous deceased racehorse (seriously). More reliable is the beer menu: 17 bottles and 16 draft beers, including the venerable Alpha King. 2020 N Oakley Ave between Armitage and McLean Aves (773-489-5471). El: Blue to Western. Bus: 49 (24hrs), X49, 56, 73. Sun–Fri 5pm–2am; Sat 5pm–3am. Average beer: $4.
This karaoke pub has the ambience of a yuppie dorm room: Posters of predictable rock icons such as Jimi Hendrix and Bob Dylan line the walls while drunken Chads belt ironic renditions of “Who Let The Dogs Out” and groups of gals get teary eyed over Pearl Jam sing-alongs. If drunken karaoke is not your thing, you can always retreat to the heavily air-conditioned pool room in back. 1610 W North Ave at Paulina Ave (773-227-7947). El: Blue to Division. Bus: 9 (24hrs), X9, 50, 72. Sun–Fri 2pm–2am; Sat 2pm–3am. Average beer: $4.
The Map Room
You couldn’t fit another beer on the killer list or another Bucktown local around the pool table here, especially on Tuesdays, a.k.a. “International Night.” This weekly party brings in food from a different ethnic spot around town—plates are free with an order of two drinks. 1949 N Hoyne Ave between Homer St and Armitage Ave (773-252-7636). El: Blue to Western. Bus: 50 Damen, 73 Armitage. Mon–Fri 6:30am–2am; Sat 7:30am–3am; Sun 11am–2am. Average beer: $4.
Catering to those who “work” odd hours (read: unemployed indie filmmakers) and a ragtag troupe of friendly regulars, this tiny (and cheap) bar-cum–liquor store is the perfect final destination for a raucous night. Doors open at the crack of dawn, and Ola, the Polish live wire who owns the joint, has been known to unlock earlier if properly coerced. 947 N Damen Ave between Augusta Blvd and Walton St (773-384-7250). El: Blue to Division. Bus: 50 Damen, 70 Division. Mon–Sat 7am–2am; Sun 11am–2am. Average cocktail: $3.50.
Phyllis’ Musical Inn
One of Wicker Park’s first spots for live music refuses to go the way of cover bands, instead 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 make for a classic summer night. 1800 W Division St at Wood St (773-486-9862). El: Blue to Division. Bus: 9 (24hrs), X9, 50, 70. Mon–Fri 3pm–2am; Sat 3pm–3am; Sun 2pm–2am. Average beer: $3. Cash only.
The bittersweet reality of great little dives is that they often lose charm when overrun by masses of clingers-on. Somehow, Rainbo has managed to remain an underground favorite. The local artists and musicians who frequent it hold on to terra firma with cheap drink in hand, awaiting a turn in the photo booth while nodding to everything from Aesop Rock to Black Sabbath. 1150 N Damen Ave between Haddon Ave and Division St (773-489-5999). El: Blue to Division. Bus: 50 Damen, 70 Division. Sun–Fri 4pm–2am; Sat 4pm–3am. Average cocktail: $4. Cash only.
It’s tough being young and fabulous. Why else would the fashionable crowd at the equally fashionable Rodan be putting back so many cocktails and black-bean arepas? Oh, right—with specials like $3 sparkling lychee drinks on Mondays, and tapioca pearls in the potent but fruity cocktails, you’d be sucking them down as if they’re going out of style, too. 1530 N Milwaukee Ave between Damen Ave and Honore St (773-276-7036). El: Blue to Damen. Bus: 50, 56, 72. Mon–Thu 6pm–2am; Fri, Sun 6pm–2am; Sat 5pm–3am. Average cocktail: $6.
Actually, this welcoming neighborhood joint is far from small—it’s a decent-sized, airy space that opens up onto a sidewalk patio. If it’s a literal name they wanted, maybe Beer Bar (named for the 90-beer- strong list), Scenester Bar (it’s not Rainbo, but close) or Cash Bar (obscure beer ain’t cheap, kids) would have been more accurate. 2049 W Division St between Damen and Hoyne Aves (773-772-2727). El: Blue to Division. Bus: 49 (24hrs), 50, 70. Mon–Fri 4pm–2am; Sat noon–3am; Sun noon–2am. Average beer: $4.
The Violet Hour
This cocktail lounge in the old del Toro space is exactly what you’d expect from a bar named after a line of T.S. Eliot poetry: pristine (the carefully constructed cocktails are excellent), pretentious (you won’t find a sign on the door—just look for the long lines) and, ultimately, completely and inarguably gorgeous. 1520 N Damen Ave between Le Moyne St and Wicker Park Ave (773-252-1500). El: Blue to Damen. Bus: 50, 56, 72. Sun–Fri 6pm–2am; Sat 6pm–3am. Average cocktail: $11.
If you’re lucky, you’ll stumble in on a night when the Anna Kournikova look-alike bartender is working, pouring vodka drinks with a heavy hand. But any night will do at this wood-paneled, Polish-owned watering hole. The old drunks are quick to challenge you at pool, and the young Poles are obsessed with the jukebox that spits out Polish versions of early-’90s American chart toppers. 1734 W Division St between Hermitage Ave and Wood St (773-486-1559). El: Blue to Division. Bus: 9 (24hrs), 50, 70. Mon–Sat 7am–2am; Sun 11am–2am. Average cocktail: $4. Cash only.