There are many reasons to visit Chicago. The Midwest metropolis is one of the only other cities in the United States that rivals New York’s cultural abundance. Sports fans have the Bears, the Bulls, the Cubs and the White Sox (beware, team allegiance runs deep here). Appreciators of art have the Art Institute of Chicago and the Museum of Contemporary Art. Food lovers will want to stop in for a deep dish pizza at Pequod’s, hot dogs with cucumbers at Byron’s are a must, as is Portillo’s Italian beef sandwich and the chile rellenos at Nuevo Leon. Most abundant of all is Chicago’s choice of bars.
Whether you want to sip beers at a 60-year-old local dive like The Old Town Ale House or you want to experience a mixological masterpiece at high-end cocktail bars like The Aviary, the Windy City has you covered. To get the inside scoop on the best bars in Chicago to drink at, we contacted some of the city’s most prominent bartenders. Here, Chicago’s best drink slingers reveal their favorite places to imbibe when they’re off the clock.
Jay Schroeder, the beverage director and partner of the mezcal-focused restaurant Quiote— and its subterranean mezcaleria Todos Santos—personally heads to Green Eye near Logan Square. According to Schroeder, the bar is “the most perfect corner bar in the known universe.” Snagging a table there is always easy (even on a busy Saturday night) and the bar not only has a quirky cast of local regulars, but there’s an abundant supply of board games to play while you drink. “Best of all,” says Schroeder, “Green Eye is one of the last places on this entire earth that you can obtain an honest-to-God, 16-ounce actual pint of quality beer for only six dollars."
From The Violet Hour in Wicker Park—a James Beard Award-winning bar and one of Chicago’s craft cocktail pioneers—Colleen Malone, the general manager, and Pat Ray, a bartender there, both frequent The Charleston and The Home of the Arts. "The Charleston has always been one of my favorite bars in the city,” says Malone. “The beer list is extensive—you can get everything from Budweiser to Mikkeller—and no one is bummed if you ask for a vodka-soda or [something more complex like a] Vieux Carré.” While The Charleston might seem like a regular, every day type of bar, it stands out because everyone bartending has a wide variety of knowledge and experience behind the bar, and all of them are welcoming. “It's a neighborhood bar where you don't have to be an actual neighbor to feel at home,” says Malone.
According to Ray, The Home of the Arts is the “platonic ideal of a dive bar.” With the decor and the vibe of a bar that has been there for more than a century, Ray says that this local dive has everything that you need from a bar: “It's dark inside, the beer is cheap and the pool is free.”
For Marina Holter, the head bartender at The Whistler—a bar, gallery and record label in Logan Square—her go-to spot when she's not working is the bistro at Red and White Wines. According to Holter, the bistro deserves more attention than it gets because of its low key atmosphere—which is conducive to great conversation with friends of hers that frequent the spot, or the strangers hanging out at the bar—and its extensive wine list. “There’s amazing natural wines that you often can't find anywhere else [in Chicago]. Anything they pour from their constantly changing by-the-glass selection is bound to be tasty.”
Another fan of Red and White is Ann Marie Meiers, a bartender at Café Marie-Jeanne, a French-style café and wine bar near Humboldt Park. Meiers says that Red and White is “one of the most intimate and tasteful bars in the city.” She also says that an essential part of what makes the wine bar so special is regular bartender Catie Olson. In addition to being “sweetly wacky,” says Meiers, Olson describes wine with “an otherworldly ease” (emphasis on otherworldly). “She's traveled wine regions extensively, focusing on natural winemakers, and her passion for the wines she serves expresses itself so joyfully and unexpectedly.” A local artist and DJ, Olson is also responsible for the eclectic playlists that play nightly at the Red and White. “She's a creative powerhouse and a blast and a half to dance with (and of course to drink with),” says Meiers.
Will Duncan, the beverage director and partner for 16” On Center hospitality collective, says his favorite neighborhood bar is The Whirlaway Lounge. “It only takes two times for you to arrive at The Whirlaway for Maria [the bartender there] to recognize you,” says Duncan. “Maria exemplifies the type of care and hospitality that’s increasingly rare in this business. She’s like your mom if your mom owned an unassuming (yet excellent) neighborhood bar.” Also of note according to Duncan is The Whirlaway’s jukebox—complete with custom CD playlists—and their birthday tradition that involves matches and a beer bottle (don’t ask, just go on your birthday and you’ll see). While this Logan Square staple isn’t the type of bar where you order a fancy cocktail, they do serve the perfect Boilermaker.
When Dylan Stewart—the manager at The Ruin Daily, a boozy coffee shop and deli—is not behind the stick you can find him at one of two bars: Bangers & Lace or The California Clipper. By sheer number of visits to the former, Stewart should probably have a plaque with his name on it at the bar. “It’s about 200 feet from the front door [of my house] and has literally become my Cheers,” says Stewart. “When I arrive, I am usually greeted by a wave from the whole staff, a cold bottle of Miller High Life and a shot of tequila before I can even sit down.” With the majority of its clientele regulars that live within a two block radius, this bar embodies the very essence of a local bar for Stewart. “It’s a cool, inviting space that is made warm by the generous hospitality of its staff and the people from the neighborhood.”
Stewart’s other regular hangout, The California Clipper, holds “a magical place” in his heart. “I’ve literally never been there without having an amazing time,” he says. “From the [bar’s] look, to the music [played there], to the vibe and hospitality, to the incredible cocktails—they’re firing on all cylinders.” Stewart first realized The California Clipper’s greatness when he randomly brought a friend there for a drink. “I arrived early, and unbeknownst to me, they were having a Honky-Tonk Christmas sing-along,” says Stewart. “Guests were singing ‘I'll have a bluuuue Christmas’ in unison. In that moment I knew I had found my new favorite Chicago bar.”
Rob Boyd, the bar manager at Dusek’s (a Michelin-starred eatery and beer house), Punch House (a secret basement bar with cocktails and food) and Tack Room (a rustic piano bar) also prefers The California Clipper. When he’s not there, you can find him at the EZ Inn—an elevated dive with daily specials, rotating DJs and an incredible jukebox. According to Boyd, both of these bars remind him of the dives that he use to frequent in his “younger crazier days,” albeit “without all the smells and sticky surfaces.”
For Annie Beebe-Tron, the bar manager at The Ladies’ Room—the bar attached to the legendary Fat Rice restaurant—her post-work drink is usually at Billy Sunday, an Amaro-oriented bar in Logan Square. According to Beebe-Tron, the drinks are creative (but approachable) and the liquor selection is diverse and interesting. She also says that Stephanie Andrews, the beverage director at Billy Sunday, “is wildly creative with her flavor profiles and her presentation.” You’ll find out of the ordinary things like a cocktail nestled in a bed of live grass to a cocktail that comes in its own decanter, ready to pour.
“There aren't a lot of people in Chicago taking both accessibility and awe to the level that she does,” says Beebe-Tron. “Whether you have a cocktail (she prefers the Tea Time, the Professor Plum and the Box Lunch) or one of the many pours of Amaro they have on their back bar, there's always something new to explore.”
When Jenee Craver, the beverage director for Sable Kitchen & Bar, has a day off you can usually find her at Best Intentions near Logan Square. Known for its “fancy cocktails” and epic patio (named the best patio bar in America by Playboy) this bar is special for Craver. “They have Angostura bitters on draft, great classic cocktails and it’s super ‘80s themed,” she says. “It’s my home away from home.” According to Craver she usually opts for a High Life with a shot of Angostura bitters or a classic Daiquiri. “I always like to peruse their online spirits list to see what new spirits they have in so that I can nerd out with the bartenders there.”
Josh Relkin, the food and beverage director for Vol. 39 and Boleo, frequents Sable Kitchen & Bar (where Craver works) as well as Best Intentions. Relkin’s love of Sable Kitchen & Bar stems from the fact that it is where he got his start as a bartender—and the fact that they make amazing cocktails. “Everything about that bar brings me to a warm and nostalgic place,” says Relkin. “The ‘War of the Roses’ [cocktail] is a Chicago classic at this point (the drink features gin, Pimm’s, lime, Peychaud’s and mint). When I was behind the bar there—making what felt like thousands of those drinks a night—it was not my favorite. But now when I go back in and sip on one, it really makes sense as to why we sold so many in a night.”
Like Craver, Relkin has an affinity for Best Intentions’ Angostura shots. “I think that Best Intentions was the first bar to have Angostura Bitters on draft,” says Relkin. “I usually start by taking a bitters shot and then move on to a well-made classic cocktail or bottled beer. They can do it all—without the pretension.”
Hero image courtesy of Sable Kitchen and Bar's Facebook page.