You already know about the 15 most hipster bars in the city, but hipsters gotta eat too, don’t they? (Seriously, DO THEY EAT???) The answer to that question is a resounding yes, especially if you visit these 15 restaurants full of mustaches, flannel, and nothing but contempt for you if you didn’t know about these places already.
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Pilsen Located down the street from local hipster holy site Thrill Jockey Records (purveyors of music from awesome indie bands you’ve never heard of), this laid-back coffee shop/café/neighborhood art gallery isn't your typical hipster hub in that it attracts a more diverse crowd. BUT THEY'RE STILL THERE.
Wicker Park Somehow this place keeps surviving year after year. Calling itself an “Asian gastropub and future lounge,” they specialize in food/drink that'll make getting into those skinny jeans still totally doable (think Thai Buffalo tofu and ginger hibiscus margaritas). Stop by for weekend specials like $6 PBR and a shot or $7 ramen while dancing/being way too cool for dancing amidst futuristic club lighting and live DJs/bands nightly.
Humboldt Park The outdoor scene here is a veritable hipster who’s-who in the summer months, when you’ll slurp down Negroni slushies and Old Milwaukee cans (for people who think PBR is “too mainstream”).
Pilsen The only thing this upscale, exposed brick-adorned Pilsen spot is missing? Fixie parking out front. Really though, you'll eat maitake mushroom faro with a side of Werp Farm radishes while checking out rotating art exhibits on the wall with your oversized frames that you don't actually need to improve your vision.
Wicker Park For those who think Big Star is sooo totally passé, this still-largely-under-the-radar local taco joint is the place to be for horchata milkshakes, Mexican Pop-Tarts, and lots, and lots, and LOTS of beards.
Ukrainian Village Located next to the most hipster music venue in the city, this place couldn’t be not-hipster if it tried. And it doesn’t. Next to Empty Bottle, stop in for some local tofu tacos and tater tot casseroles. Hipster bonus: it’s BYOPBR!
Pilsen Dusek’s earns hipster street cred you've probably never heard of thanks to its prime location within the hipster Holy Trinity that includes Dusek's, downstairs punch bowl haven Punch House, and nearby venue Thalia Hall (owned by the Empty Bottle/Longman & Eagle dudes). The $4 Schlitz and bourbon boilermakers don’t hurt either.
Bucktown The only place to make both our hipster bar and hipster restaurant list, Handlebar and its mustachioed bike messenger vibe, vintage concert posters, and cool back patio feels like the kind of place you'd find lots of people with, well, handlebars. The vegan-friendly menu helped this spot reach the Top-10, but it's the house rule (“We like loud music and cannot turn it down”) that earns Handlebar Top-5 status.
Logan Square This new entry to the hipster restaurant scene has risen through the ranks quickly, thanks to its “Bartoon Brunch,” where you can watch animated comedy like Bob’s Burgers, American Dad, and Futurama while drinking Green River floats and PBRs. Check out occasional live indie bands like White Mystery while dining on classic double patty griddle burgers in booths that look like they were crafted in the console of some futuristic video game.
Logan Square Owned by the same crew as Parts & Labor (as well as established hipster hubs like East Room and Simone’s), Boiler Room’s claim to fame is its $8.50 PB&J special that include a slice of pizza, PBR tallboy, and shot of Jameson. Where they rack up major hipster bonus points, though: boozy Jameson soft serve, PBR meatball sandwiches, and something called PBR bingo -- where you can win prizes including PBR dartboards and PBR bag toss games. PBR. PBR. PBRPBRPBR.
Logan Square So. Many. Hipster. Boxes. Checked. Too many to be dislodged from its top ranking. 1) PBR breakfast with a can of PBR, 2) 300+ whiskeys, some of which can be yours in the form of $3 shots, 3) an upstairs B&B with rooms outfitted with Apple TV, plus vintage cassette tapes consoles WITH mix tapes, and 4) the next-door Off-Site Bar, a garage of Malört and $1 Old Milwaukee cans.
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Jay Gentile is Thrillist’s Chicago Editor and he could eat at Lula Café every day of the week. If he was cool enough. Follow him @ThrillistChi.