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Looking to sing bleary-eyed karaoke until 4am? Congratulations: you’ve found your Shangri-La. Once you’re buzzed in, grab a Zywiec and flip through karaoke DJ Fred’s massive collection of songs until you’ve found a winner (and no, you don’t sound as awesome as you think). If you feel like acting like a total asshat and falling down all over the stage, be warned: Alice and Fred are more than happy to cut you off. But if you’re cool, they’re cool.
Grandma knows how to throw one hell of a basement rager. If your grandma happens to be Rose, of course. Tear through pitchers of Old Style as you wait for the Tamale Guy, shoot some stick while playing cool jams, or just chill on the couches that have seen more than their fair share of tomfoolery over the years.
Plenty of places in Logan Square try to be cool. Whirlaway just is. Whether on an awkward Tinder date or bombing in with a group of sweater-wearing Hawks fans, you’ll always find a spot here with a colorful cast of regulars. Chat with the always-friendly Maria, play Connect Four, or just sit back and watch the game. Any game. It doesn’t matter.
If you’re the type that brings his own ping-pong paddle to the bar, 1) you’ve got serious problems; 2) you’ve found your new home at Happy Village, where epic games of pong go down in the back room while outside you can chill in one of the best patios in town (although not quite as cool since they paved it). Either way, you’ll need to work extra hard to have a bad time here.
Yes, something smells here. It’s the musty smell of fun. While the classic neighborhood dive recently made a cameo in the TV show Sirens, it’s still pretty much required partying for anyone within spitting distance of its iconic sign. It’s got all your dive bar basics covered: cheap drinks, good jukebox, and pool, with the bonus elements of open mic night weirdoes and a giant Elvis.
As Division Street continues to get fancier and fancier (even Smoke Daddy has recently seen upgrades), Goldstar continues its defiance by staying as divey as ever. While nearby Rainbo, Zakopane, Phyllis’ and Rite Liquors are also more than worthy dive stopovers, Gold Star is like a step back in time where nothing changes except everything around it. Which, in this case, is definitely a good thing.
Frequented by everyone from serial killers Jeffrey Dahmer and John Wayne Gacy to punk bands Against Me! and The Lawrence Arms, L&L retains its classic no frills, shot-and-a-beer appeal despite the endless crop of idiot bars surrounding it in the dangerously closing-in confines of Wrigleyville. While you might encounter a wayward tourist every now then looking for a party, most are probably too scared to enter. Which is the way L&L likes it.
A country bar? In Chicago? On paper, Carol’s shouldn’t work. But late nights don’t happen on paper. They happen at this friendly off-the-beaten path honky tonk that’s definitely seen weirder shit than you and your imbecile friends since it opened in 1973. If you think you hate country music -- which is a perfectly acceptable thing to hate -- come to Carol’s and then come talk to us.
Made famous as Vince Vaughn’s favorite hangout in The Break-Up, this cozy brick shack was cool before Pilsen was cool. With a vintage photobooth and old rifles on the wall, it also boasts a surprising quality range of food options, from potato and cheese pierogi to beer-battered cod sandwiches. Because sometimes, late nights require need more than a jar of peanuts.
There's mismatched furniture, the backstage area is a total cave, and the bathroom looks like someone shat graffiti all over it. But, but, but, they've got some nice beers! While its hipster meter is precariously high, free live music is nothing to sneeze at either.
Blatantly disregarding Chicago’s no-smoking laws, this, um, smoky(!) dive sports neon signs, kitschy posters, and a payphone focal point reminiscent of the 1960s. Guzzle dirt-cheap beer and nosh on chips or hard boiled eggs for less than a buck. If you’re wondering why the hell you can smoke here but nowhere else in the city, don’t ask.
This 50+ year-old saloon is one of the few places in Chicago you can simultaneously drink and get a poli-sci lesson: the walls are covered with portraits of nude politicians (hello, gun-wielding Sarah Palin with nothin’ but red heels on). Whether you’re partying with grizzled old timers or unwinding Second City tourists, there’s always something interesting going on.
1. Happy Village1059 N Wolcott Ave, Chicago
2. Old Town Ale House219 W North Ave, Chicago
3. Rose's Lounge2656 N Lincoln Ave, Chicago
4. Richard's Bar491 N Milwaukee Ave, Chicago
5. L&L Tavern3207 N Clark St, Chicago
6. Gold Star Bar1755 W Division St, Chicago
7. Cole's2338 N Milwaukee Ave, Chicago
8. Skylark2149 S Halsted St, Chicago
Happy Village is a neighborhood bar located in Ukrainian Village. While it may be unassuming from the outside, the interior is sleek and lively, and there’s a back room housing two ping pong tables. The backyard beer garden -- fully equipped with a pond and goldfish -- is open year-round, though let’s face it, this is Chicago. The neighborhood bar is cash only, but with daily specials, perpetually cheap beers (Old Styles for just $2… again, the Chicago thing), and free ping pong, a visit to happy village will leave your wallet happy, too.
Old Town Ale House is an iconic Chicago dive bar whose crowd varies between comedians from nearby Second City, hipsters, tried-and-true regulars, and tourists (due in no small part to the bar's feature on Anthony Bourdain: Parts Unknown. ) The jukebox, which is usually playing jazz, rules the show, but don't be surprised if one of the bartenders puts on some opera to water down the crowd. The wall is covered with funky paintings of everyone from longtime regulars to celebrities and politicians... case in point: a portrait of a naked Sarah Palin holding a rifle.
Through the screen door of Rose’s Lounge in Lincoln Park, you’ll find mismatched lounge chairs, couches, and dining room table sets, wood-paneled walls, and christmas lights year-round for a pop of light and color in an otherwise musty, basement-reminiscent dive bar. It’s been run by a woman named Rose since the late 70s, which seems to be the last time the bar’s interior was designed. The mugs are frosted for your pints of Old Style, which run for just a couple dollars, and is the perfect beverage to pair with a game of billiards.
First thing's first: smoking is legal -- and prevalent -- inside the confines of West Town's beloved Richard's. That said, if smoke bothers you, feel free to stop reading, but if you like fun, don't. Yes, you'll be drinking beer from a bar studded with ash trays, but it's cheap. And yes, you'll be dancing through foggy clouds of smoke, but to the music you've selected on the jukebox. It's divey, dark, and a damn good time... just know that a shower is in your immediate future.
Lakeview's L&L Tavern has a dark and storied past, but remains one of the city's more interesting dives because of it. It’s rumored that both Jeffrey Dahmer and John Wayne Gacy frequented the tavern, the former scoping out his next victim through the window facing the street, and the latter in a full clown suit. So… what are you waiting for? Sip your PBR tall boy and realy familiarize yourself with the serial killers by sitting in the very bar -- maybe even the very chair -- they once occupied. Or just go because the beers are cheap, that works too.
Gold Star's got something for every dive-lover; they've got free popcorn, cheap booze, and a jukebox.
Cole's is a down-home dive serving up cheap brews, great tunes, and a stellar crowd.