Flickr/Laurie Chipps
Simone's
 
Facebook/The-Continental
 
Flickr/Connie Ma
 
Flickr/Kara Brugman
Flickr/Gino
Flickr/Clint McMahon
Flickr/Seth Anderson
Flickr/Eric Allie Rogers
Facebook/RogerTinoMorales
Flickr/Chris
Flickr/Devin Hunter
Flickr/Alex D. Stewart
Maria's Packaged Goods
 
Flickr/Eric Bartholomew
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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...)