50 unknown bars: Unsung but lovable dives, lounges and taverns.
Chicago dives, lounges and taverns.
BLACKHAWK VFW POST 7975
With a drop ceiling and offices lining one side, the bar that vets open to the public on Friday and Saturday nights for karaoke has all the charm of a middle-school classroom. Luckily, sassy karaoke MC Bill Nowlin fills the stark room with his smooth singing voice, and if he likes your pipes, you earn a ring from his bell. Cool your jets with a $3 gin and tonic till the party people arrive after midnight. Extra shot Free bowls of hot, buttery popcorn fortify you to belt out a few more songs. 1000 N Milwaukee Ave (773-252-5338).—Laura Baginski
The North Side’s littered with Cubs bars, but an anti–White Sox bar? That’s an oddity—as are some of the patrons at this dark, tchotchke-stuffed dive bar. Bait the Rodney Dangerfield–like proprietor on what he thinks of the Sox and he’ll tell you he doesn’t follow minor league teams as he reaches for the pull on a neon sign that buzzes to life with the words SOX SUX. Just don’t show up before 10:30pm—Ray’s “retired” from working the bar full time. Extra shot The irregularly scheduled Ray’s Tap Reading Series packs the place with young literary types every other month or so. 3049 N Kimball Ave (no phone).—Martina Sheehan
Expect to get manhandled at the Manhandler Saloon. Tucked among the trendy shops in the heart of Lincoln Park, this 30-year-old country-western hole-in-the-wall is stocked with bottled beers, rugged barstools, gay porn on the TVs and plenty of middle-aged discreet men. Patrons are on the down-low and don’t converse much, so if you just stumble in off the Boystown stretch, you might feel like a fish out of water. Extra shot The crowd gets more friendly in the back shed, where men get a better “feel” for each other. 1948 N Halsted St (773-871-3339).—Mark Bieganski
One of the few bars on Devon Avenue’s Indo-Pak corridor, Cary’s has all the markings of a dive except one: Instead of Old Style taps, you get three chalkboards of impressive beer options, including New Holland’s Mad Hatter and Three Floyds’s Robert the Bruce. Monthly karaoke nights and occasional live-band appearances on the tiny stage keep the place interesting, but the real entertainment is interacting (or ducking interactions) with the bar’s cast of characters. Extra shot The pool table is free. 2251 W Devon Ave (773-743-5737).—Angela Barnaby
This family-owned sports pub has operated since 1951 on a back street of Pilsen, kitty-corner from the twin spires of St. Paul Catholic Church. A mix of the neighborhood’s Latinos and Anglos come out for cheap burgers, chicken sandwiches and chops, plus daily drink specials like $4 pints of Spaten Oktoberfest. The microbrew selection is impressive, including selections by Dogfish Head and Magic Hat on tap. Jerseys autographed by Paul Konerko and Joe Montana, numerous Blackhawks photos and free pool make this a comfortable hang for superfans. Extra shot Don’t miss the video beer-pong machine. 2058 W 22nd Pl (773-847-5515).—John Greenfield