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...

Flickr/Laurie Chipps

15. California Clipper

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.


14. Simone’s

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.


13. The Continental

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.

Flickr/Connie Ma

12. Skylark

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.

Flickr/Kara Brugman

11. Hungry Brain

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.


10. Bar DeVille

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.

Flickr/Clint McMahon

9. Club Foot

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.

Flickr/Seth Anderson

8. Innertown Pub

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.

Flickr/Eric Allie Rogers

7. Handlebar

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.


6. East Room

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.


5. Empty Bottle

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.

Flickr/Devin Hunter

4. Rainbo Club

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.

Flickr/Alex D. Stewart

3. The Burlington

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.

Maria's Packaged Goods

2. Maria’s Packaged Goods

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.

Flickr/Eric Bartholomew

1. The Whistler

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.

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1. California Clipper 1002 N California Ave, Chicago, IL 60622 (Humboldt Park)

California Clipper, an iconic Humboldt Park hideaway, is still as charming today as it was in the 30s. Though more recently revived by Hogsalt’s Brendan Sodikoff, California Clipper’s dim, red lighting and old-school jukebox help the decades old dive retain its vintage reputation. As well does the beverage list, which is over 20 pages long, designed with the30s in mind, and features staff favorites, punches, long drinks, shaved ice, and ice cream drinks, as well as beer, wine, and other spirits. Enjoy a bowl of punch over conversation, or grab a can of beer to and listen to the live music, multiple nights a week.

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2. Simone's 960 W 18th St, Chicago, IL 60608 (Pilsen)

From the Danny's/Northside/Black Beetle team and housed in a 100-year-old building, Simone's is a sprawling, laid-back bar & grill whose eco-friendly credo actually plays out cool, with a wire-fence-wrapped elevated DJ booth, barstools made from old doors, booths constructed from vintage pinball machines and old seatbelts, and a J-shaped bartop made from wooden bowling lanes -- so you can throw back Turkeys where others have thrown them.

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3. The Continental 2801 W Chicago Ave, Chicago, IL 60605 (Humboldt Park)

Head to this divey Humboldt Park bar for a great patio space, tight (but friendly) quarters, and a prime location next to a chicken shack.

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4. Skylark 2149 S Halsted St, Chicago, IL 60608

Not only does this dive bar have some of the best tater tots in the area and an awesome beer list -- it's got a photo booth too. Warning: cash only.

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5. Hungry Brain 2319 W Belmont Ave, Chicago, IL 60618 (Roscoe Village)

If you head to this Roscoe Village drinkery, you're guaranteed to get your fill of indie rock, colorful Christmas tree lights, and beat-up antique sofas (not to mention a good time and cheap drinks).

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6. Bar DeVille 701 N Damen Ave, Chicago, IL 60622 (Ukrainian Village)

Craft drafts, liquor-forward libations, and hip environs -- such are the makings of a great night out at Bar DeVille. Manned by veteran bartender Brad Bolt and Chicago hospitality gurus Matt Eisler and Kevin Heisner, Bar DeVille offers expertly mixed cocktails, whether familiar classics or original favorites like The Hard Sell, made with Beefeater gin, Malort, St. Germain, and lemon. Come for the drinks, stay for the ambience: from the live DJ, pool room, and photo booth, to the Art Deco-inspired bar and refurbished Victorian sofas, this trendy neighborhood watering hole is frequented by industry folk and locals alike.

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7. The Handlebar 2311 W North Ave, Chicago, IL 60647 (Wicker Park)

This hipster-approved restaurant and bar in Wicker Park serves a vegan and vegetarian menu of American classics. Breakfast is served daily until 3pm (don't worry, there are plenty of egg dishes) but expect seitan sausage instead of bacon. The rest of the menu (it serves lunch and dinner too) is filled with meat-free bar bites like fried avocado tacos, chili cheese fries (available with vegan queso), soy-based sloppy Joes, all of which taste especially good when paired with a drink in the beer garden.

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8. East Room 2828 W Medill Ave, Chicago, IL 60647 (Logan Square)

Follow a single red lightbulb to an unmarked door off Milwaukee Ave. in Logan Square, and you’ll eventually find your way into the music venue and speakeasy that is East Room. Though its entry may lead you to believe it’s on par with the rest of the pretentious, unmarked cocktail bars of the world, one step inside and those expectations shatter. East Room is a beer-and-a-shot joint with live music, 30 beers, and 40 whiskeys to choose from. And it’s cash only, but show your receipt from the on-site ATM to the bartender… it’s your ticket to a shot of whiskey, on them.

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9. Empty Bottle 1035 N Western Ave, Chicago, IL 60622 (Ukrainian Village)

Empty Bottle's got awesome live music, a photobooth, and a cheap booze selection.

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10. Rainbo Club 1150 N Damen Ave, Chicago, IL 60622 (Ukrainian Village)

Around since the 1930's, this Wicker Park dive is notorious for its crowd of beanie-clad, PBR-guzzling hipsters, engrossed in competitive games of pinball. Once home to a series of burlesque shows, the dimly-lit space is now a stomping grounds for Chicago's young and fashionable (and arguably pretentious) imbibers, gathering around the island-like, shamrock-shaped bar to order well-drinks and remarkably cheap draft beers. The place is hard to miss with an enormous L-shaped neon sign hanging above the ramshackle facade, and the interior features an equally retro juke box, red vinyl booths, and a fully functional photo booth (much to the delight of many-a-hipster). With an eclectic soundtrack, a constantly rotating selection of art work on display, and a bar that serves until 4 am, the places rarely has open seats.

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11. Maria's Packaged Goods & Community Bar 960 W 31st St, Chicago, IL 60608 (Bridgeport Sox)

Maria's is an awesome dive bar with eclectic selections and friendly staff.

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12. The Whistler 2421 N Milwaukee Ave, Chicago, IL 60647 (Logan Square)

Started by two indie label owners/members of a punk acapella group (seriously), Whistler's a music venue so great, you'd happily hang out when no bands are playing: decked out w/ exposed brick, an L-shaped walnut bar top, reclaimed church pews and chairs with hymnal holders on back, and an intimate, nicotine-friendly back patio, where you can indulge in the habit that'll one day ensure daily prayer.

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13. Club Foot 1824 W Augusta Blvd, Chicago, IL 60622 (Ukrainian Village)

If you're ready to get a little (or a lot) weird, you're ready to hit up Club Foot. Get your dance on to some punk music while enjoying the strange decor and unique crowd.

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14. Innertown Pub 1935 W Thomas St, Chicago, IL 60622

Innertown Pub is home to one of the best hipster dives in Chi. Sidle up with a cold brew, cheap 'tail, or hit some pool and darts in the back.

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15. The Burlington 3425 W Fullerton Ave, Chicago, IL 60647 (Logan Square)

This bar in Logan Square is one of Chicago's most authentic of hipster bars, thanks to obscure bands playing every night and an insider’s vibe that makes you feel like this is where they shoot indie rock videos (which they totally do...)



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