So you know how ESPN has power-rankings of sports teams? If you’re a hipster, of course you don’t. But that’s okay, because we’ve taken it upon ourselves to power-rank the top 15 hipster bars in a city that's overflowing with hipsterdom. Although, we assume that now that you know this, they're no longer hipster...
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Humboldt Park It doesn’t get much more hipster than taking a sip from a Rusty Nail (Scotch, Drambuie) served at a 1937 Brunswick bar, surrounded by enough dim red lighting to get a Chinese takeout joint evicted from Amsterdam’s Red Light District. Board games, kitschy lamps, and an allegedly haunted atmosphere round out the classic hipster vibe. As do its patrons.
Pilsen If the Divvy station out front isn’t a good indication of this Pilsen bar’s hipster bona fides, it might be time to grab a seat in the back room called “The Lab”, and survey your surroundings -- which may or may not include a rooftop herb garden, graffiti street art, and a bar top made from an old bowling lane. It’s as good a place as any to dissect the latest Pitchfork review.
Humboldt Park When hipsters want to drink after 2am, they don’t go to Tai’s Till 4. They go to this tiny little strip of real estate next to a chicken shack in Humboldt Park, where the cramped quarters mean you're basically forced to make friends. Quickly. It’s a nice alternative to the traditional cheese of 4am bardom, with a great outdoor patio that finally makes wearing that beanie kinda worthwhile.
Pilsen 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 simply tearing open a bag of Doritos would be totally un-hipster.
Roscoe Village Hipsters are into their indie rock. This much we know. But did you know some are also into jazz? Yes, the music genre that originally coined the term comes to life at this delightful little dive off Belmont, complete with colorful Christmas lights and beat-up antique lounge sofas. See top-tier local jazz bands, or just set up shop at the Galaga machine, aka hipster Pac-Man.
Ukrainian Village Driving up from the United Center to Wicker Park, blink and you might miss this bar. And that’s how hipsters like it. It’s famous for Moscow Mules and an awesome back room where everything from dance parties to comedy sets go down, in what looks to be some lost Medieval parlor room. You can also shoot pool beneath a massive set of animal antlers that will go nicely with your flannel shirt and skin-tight jeans.
Ukrainian Village Need proof that hipsters like to get weird? Two words: Club Foot. If you’re into strange flotsam hanging from the ceiling (including blow-up balloons of French fries and a sticker-plastered bathroom with a weird elevated toilet), this is the place for you. If not, do a shot, wander over to the cage-like DJ booth, and ask them to play some punk. They’ll be more than happy to oblige. Or not.
East Village Yes, something smells funny in here. Don’t worry. You get used to it in this hipster’s attic lined with unusual wall trappings, such as a Mona Lisa traced in Christmas lights. Stop by on open mic night for some real entertainment, or just hangout in front next to the bike rack and bum a Parliament from someone in a Minor Threat t-shirt.
Bucktown When a place has an event called “Bike Messenger Mondays” (where bike messengers get free fries), you know their hipster index is probably pretty high. Couple that with an all-vegan menu and ubiquitous hipster band posters, and you’ve got yourself one of the city’s most mustachio'd hubs, with a classic back patio that feels like your buddy’s backyard. You know, the cool one.
Logan Square Hipsters love to be the first to know about the latest, cool new thing. And East Room is one of those things. With an unmarked entrance only accessible by alley, and random art films projected on walls, this place is “so hot right now” in the hipster community, were one of those to even exist (they don't organize, bro). Simply measuring by the amount of PBR consumed alone, this place could win an award. If hipsters were into awards.
Ukrainian Village While this is more of a music venue than the traditional “bars” associated with this list, it doesn't change the fact that this is the kind of place where you shoot pool with the dudes from Interpol and swap obscure vinyl at handmade markets. Plus, you’ll also see bands like Arcade Fire here before they get big. And no longer cool.
Wicker Park This legendary local dive is famous as the one-time stomping ground for local ‘90s greats like The Smashing Pumpkins and Urge Overkill. And it hasn’t changed much since then. Enter to find a tripped-out mashup of gold-framed antique art, deer heads, and cheap booze. Gotta have cheap booze.
Logan Square While technically any bar in Logan Square could make this list, this late-night haunt is one of the most authentic of hipster mainstays, with obscure bands playing nightly and an insider’s vibe that makes you feel like this is where they shoot indie rock videos (... because they do). They’re also putting on the Neon Marshmallow Fest -- the hipster’s anti-Lollapalooza -- over Lolla weekend.
Bridgeport The publisher of local hipster bible Lumpen is now the co-proprietor of this recently revamped South Side tavern, which's more like an evolving art project than a bar. Curating some of the best DJ nights in the city paired with 500 craft beers and a weekly Korean-Polish BBQ held in the back patio, this neighborhood bar/liquor store is a fanny pack-wearers oasis in a sea of blue collars.
Logan Square Part-cocktail bar, part-record label, part-art gallery, and part-live music venue, this place checks all the essential hipster boxes. Sip a world-famous cocktail poured from top local mixologists and listen to tracks from the in-house record label, all while packing yourself into this tiny 74-capacity hipster VIP lounge. Because 75 people would be way too mainstream.
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Jay Gentile is the publisher of Chicago INNERVIEW Magazine and a Chicago-based freelance writer who does his best thinking in bars, hipster or otherwise. Follow him @InnerviewMag.