The best bars in Wicker Park and Bucktown
You couldn’t fit another beer on the killer list or another Bucktown local in this cozy tavern on the occasional Tuesdays when the bar unveils new or limited releases of specialty beers. The menu here is expansive, and the bartenders are more than willing to help you find a New England-style IPA or nitro stout that fits your unique tastes. If you’re a more low-key drinker but like the vibe, stop by in the morning when the Map Room functions as a coffeehouse.
This cocktail lounge is exactly what you’d expect from a bar named after a line of T.S. Eliot poetry: pristine (the carefully constructed cocktails are excellent), pretentious (you won’t find a sign on the door, though lately the no-phones policy has relaxed) and, ultimately, completely and unarguably gorgeous. Make sure to admire the mural (which changes every month) on the front of the building while you're waiting in line.
The bittersweet reality of great little dives is that they often lose charm when overrun by masses of clingers-on. Somehow, this spot on the edge of Ukrainian Village and Wicker Park has managed to remain an underground favorite. The local artists and musicians who frequent it hold on to terra firma with cheap drink in hand, awaiting a turn in the photo booth while nodding to everything from Aesop Rock to Black Sabbath.
What do you get when you combine 28 craft beers on tap with 47 1980s and ’90s arcade games, from NBA Jam to Super Mario Bros. to Mortal Kombat? A packed room crammed with date nights, big groups and sheepish men in their early thirties who look as if they’ve never been in a bar before.
This Bucktown dance bar has a line on Friday and Saturday nights that’s worth the wait. Half bar and half apartment, the space will make you nostalgic for the house parties of your college days, if you aren’t still living them. Grab a glass of whiskey or dirt-cheap PBR and elbow your way into the crowd packed wall-to-wall with hipsters. Rotating DJs play everything from throwback 80’s hip-hop to Brazilian samba, and there are plenty of dark candlelit corners to canoodle in if you hit it off with someone on the dance floor.
Not feeling Subterranean’s music for the night? Can’t take the hipper-than-thou crowd at Rainbo? Prefer a place less clubby than Debonair? Head to this low-key sanctuary in the otherwise oft-pretentious Milwaukee-North-Damen intersection. No one’s trying to out-cool anyone here (though late at night, they’re definitely trying to pick each other up), so feel free to strike up a conversation with a stranger over some tasty late-night bar eats, served until the wee hours of the morning.
Situated on the 13th floor of the Robey hotel, Up & Up is a cocktail lounge with quite a view of the distant Chicago skyline. Be prepared to wait in line before heading upstairs to sip Scotch and gaze at the twinkling lights—the bar only seats 35 people, making it one of the more exclusive rooftops in the city.
Late-night drinking options near the Western Blue Line station used to be slim, but Remedy Bar provides your 4am fix. Step inside and you'll find eight craft beers on tap, a formidable bottle list and a jukebox stocked with everything from John Lee Hooker to the Strokes—perfect for impromptu post-2am dance parties.
There's a decent number of sports bars in Wicker Park, but we're partial toward the Fifty/50, which is situated in the heart of the madness that is Division Street. This clean, TV-equipped bar has some of the best wings in town, offering breaded, boneless and smoked options smothered in sauces like buffalo, spicy garlic and sweet chili cilantro. If wings aren't your thing, opt for vegetarian-friendly dishes like deep-fried cheese curds, beer-battered pickles or the Caesar, lime and avocado salad. Wash it down with wines by the glass, plenty of beer options and curated collections of bourbon and Scotch.
This craft beer-and-sausage themed bar took over the former Bin 36 space, and there’s not a hint left of the original wine bar among the sleek wooden tables and huge TVs lining the room. A pair of gigantic screens display the current tap list and statistics for beer left in each keg, in case you might miss out on the last dregs of a rare pour. With a local-heavy selection, there’s a draft for everyone, and five wines on tap if beer isn’t your thing. The food menu is composed of classic bar snacks and a selection of house-made sausages, like cheese curds, deep fried in a light tempura batter, and a juicy steak and ale sausage.
The low-key bar, decorated with Oriental rugs, a fox head and rounded burgundy leather booths, is a comfortable spot with a strong selection of draft and canned beers and approachable cocktails, like Gold Bullets & Vampires, a gin cocktail mixed with apricot cordial and Vander Mill Totally Roasted Cider, a sweetly spiced drink that manages to still be refreshing. The bar's glowing Old Style sign beckons passengers arriving at the nearby Damen Blue Line station, so show up early in the evening if you want o grab a table.
At this bar by the owners of Bar DeVille, “bangers” stand for sausage (we dig the Chicago-style Vienna Beef over the fancier brat sandwiches), and “lace” for “Brussels lace,” i.e., beer foam on the edge of a glass. The stellar draft selection, two-ounce sample options and knowledgeable staff draw in a mix of beer geeks and neighborhood clientele.
Chicago's first self-serve bar offers 32 beer, eight wine and 12 cocktail taps accompanied by a friendly staff of bartenders to guide guests through the experience. For those nights when you don't feel like drinking, choose from kegs of kombucha, craft soda and local cold-brew coffee. The Wicker Park space also boasts a curated food menu with options like grilled cheese with chipotle cheddar, corned beef sliders, cheese fondue and gelato.
Adjacent to the Wicker Park branch of Cheesie's Pub, Whiskey Business offers copious amounts of ’80s nostalgia without the noisy video game cabinets that clutter Chicago's barcades. This is the kind of place you go to drink a MacGuyver cocktail, watch Ghostbusters and eat a burger stuffed with crab cakes. The rooftop patio makes this a popular destination to knock back fluorescent frozen drinks and try to sip your way back to the halcyon days of your youth.
Some nights, it might just be you and the bartender at this wood-paneled relic; you pour your heart out, while they pour vodka drinks with a heavy hand. The old drunks are quick to challenge you at pool, and the young Poles are obsessed with the jukebox that spits out Polish versions of early-’90s American chart toppers.