The best bars in Wicker Park and Bucktown

This cocktail lounge is exactly what you’d expect from a bar named after a line of T.S. Eliot poetry: pristine (the innovative and carefully constructed cocktails are excellent), pretentious (you won’t find a sign on the door) and, ultimately, completely and unarguably gorgeous. Make sure to admire the mural (which changes often) on the front of the building while you're waiting in line.

You couldn’t fit another beer on the killer list or another Bucktown local in this cozy tavern. 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 well-traveled vibe, stop by in the morning when the Map Room functions as a coffeehouse.

As a newbie to the Bucktown bar scene, Truce came out the gate swinging as a coffee shop by day and cocktail bar by night. The walk-in only establishment aims to embody the spirit of a neighborhood bar, with an elevated drink menu to keep patrons coming back. You can't go wrong with the striking Absinthe Frappe with a fluffy pandan whip, but the chai daiquiris and lemond pound cake martinis are just as delicious. 

Situated on the 13th floor of the Robey hotel, the Up Room is a cocktail lounge with quite a view of the distant Chicago skyline. The intimate indoor seating is limited, but try to grab a coveted section inside the Robey spire on the outdoor rooftop. While the spirit list is sure to excite whiskey aficionados, the seasonal cocktail menu still has something for every palate.  

Not feeling Subterranean’s music for the night? Can’t take the hipper-than-thou crowd at Rainbo? Didn't budget for a night out at Violet Hour? 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.

Lottie's story goes all the way back to the 1930s when the beloved sports bar was just a grocery store. Today, it's spread its wings to become host to a crowd of weekly trivia fanatics, some of the best game day celebrations in the area and an impressive $2 taco.

Venture through a petite record shop storefront in Wicker Park to discover Dorian’s, a cocktail bar built around music (or behind music, if you want to get literal). The elegant space boasts an Italian-made hi-fi sound system for vinyl DJ nights and a stage for live music—where the bar has hosted performances from luminaries like Jeff Parker and Makaya McCraven—plus a narrow menu of house cocktails perfect for sipping while you listen. 

Another historic neirghborhood dive, the Charleston is a tucked away gem of Chicago's yesteryear. The no-fills tavern has morphed into quite the scene for great cocktails and live music, with a fresh crowd filling the seats at Hoyne and Charleston every night. 

This three-room inn at the center of Bucktown doubles as a just-as-charming community watering hole. With Chicago and Midwest breweries on tap, you're sure to find highly sought-after local brews. The Leavitt Street kitchen boasts a killer smash burger that is paired perfectly with dessert sweets from Bang Bang Pie. Cocktails are rotating, but whatever you choose is sure to go perfectly with the gigantic outdoor patio (one section is tented and heated for year-round fun). 

Let the libations invigorate your competitive spirit at the Wicker Park location of this beloved arcade bar. With more craft beers than you can count and dozens of throwback arcade games including NBA Jam and Mortal Kombat, it's the perfect place for an eventful first date or end-of-the-week catharsis with friends.

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 six 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.

The boys behind Estelle’s and Alive One decked out this dark-red room with low-key, classy decor and a jukebox that floats easily between Otis Redding and Arcade Fire, creating an aura that brings in every kind of character. The pool table front and center along with Wednesday night comedy shows only adds to appeal of this neighborhood jewel. 

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 Una Stanza, a gin cocktail mixed with orgeat syrup (almonds and sugar mixed with rose/orange water) and Liquid Swords, a mezcal drink that packs a punch with smoked jalepeño liqueur and cherry juice. 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 to grab a table.

At this bar by the owners of Bisous and other popular watering holes, “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, refreshing array of rotating cocktails and knowledgeable staff draw in a mix of beer geeks and neighborhood clientele.

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 younger crowd is obsessed with the jukebox that spits out Polish versions of early-’90s American chart toppers.

This amber-tinted lounge is certainly chic and a bit upscale, but somehow lacks the stuffiness usually associated with those spots. Its restaurant-worthy menu is enhanced by the attentive, conversational staff and colorful paintings by local artists that dot the bar's exposed-brick walls. Chow down on your classic bar food from the kitchen and taste test any kind of mule (Moscow, Mayan, Kentucky, etc.) you can think of.