Chicagoans are quite spoiled when it comes to booze: The city is home to some of the country’s most creative distillers and breweries, making it an incubator for top talent. Every year for Time Out Chicago’s Bar Awards, we enlist a panel of insiders to help us honor these craftspeople and the bars behind them. The 2018 winners read like a checklist of must-try Chicago watering holes—from a jazz club that’s been serving stiff drinks since 1907 to a mescal-filled basement spot that’s become a fast favorite. Without further ado, let’s give it up for this year’s winners.
RECOMMENDED: Take a look at the 2018 Bar Awards finalists
2018 Bar Awards Winners
Why we love it: It’s hard to believe that Lost Lake opened on Diversey Avenue just three years ago. Helmed by Paul McGee and Shelby Allison, the tiny tiki bar has reached institution status in record time. How? By going beyond banana dolphins and bendy straws (though there are also plenty of those!) and pushing the boundaries on what rum mixed with fruit juice can taste like. With every new year and each new menu, we continue to be blown away by Lost Lake’s talented team, dangerously delicious drinks and Asian-inspired bar snacks.
From the panel: “Take a moment and adjust your focus away from your perfectly Instagrammable cocktail. Do you notice how much the staff here cares? Do you see how, for them, it’s not a job but a lifestyle? Do you see how everyone is genuinely smiling? Isn’t the food delicious? Where are we—Chicago? Really? Incredible.” —Brenton Engel
Why we love it: You want legacy? This Uptown jazz bar has it in spades. The space opened in 1907, but most of Green Mill’s rich history was laid during Prohibition, when Al Capone and other gangsters frequented it and reportedly used a series of underground tunnels to ferry booze into the joint. Though it has since shed any nefarious ties, you can still grab a stiff drink and take in jazz tunes from Capone’s choice booth, which conveniently affords views of both the front and back doors.
From the panel: “It’s timeless, historic and fun. It’s the type of bar that allows me to brag about Chicago as a city. Green Mill’s character is earned—no new bar could re-create it. Its walls whisper tales of the past, and you feel like you’re sharing in a such a cool piece of history while you’re there.” —Danny Shapiro
Why we love it: This mysterious Logan Square booze den stands in stark contrast to Chicago’s plethora of bright, Instagram-friendly bars. Guests enter the room through an alley and descend a staircase to find the 40-seat interior. The jolting focal point of the dimly lit bar is a neon sign that reads Weddings & Funerals. Put away your phone and order from a menu of lesser-known classic cocktails as you sink into the sultry space.
From the panel: “There’s not a sexier place to hide from our Twitter-crazed society and forget what time or day it is.”—Brenton Engel
Why we love it: Situated near a stretch of Wicker Park that constantly churns out shiny new bars and restaurants, Rainbo Club is an incorruptible constant. The red neon sign beckons from blocks away, pulling patrons into its no-frills, no-bullshit space to down a shot and a can of something cheap in its coveted red booths.
From the panel: “Since the ’80s, owner Dee Taira has been the bar matron to the motley crew of scalawags, musicians and curmudgeons that populate the bar staff and sometimes live in her building. When they finally admit that they remember your name, you feel super special.”—Nandini Khaund
Why we love it: Quiote has long been on our radar for its modernized yet respectful plays on Mexican cuisine, but it wasn’t until late last year that Jay Schroeder (Mezcaleria Las Flores) gave the downstairs mescal bar a life of its own. If you love the agave spirit and traditional Mexican flavors—think chilies, cacao and tamarind—Todos Santos will be your new favorite hideout. And if you don’t, well, you should rethink your priorities over a drink at this rathskeller spot.
From the panel: “Todos Santos is an oasis: The purest, funkiest and most divine mescals await in pristine bottles behind the bar. When I’m craving mescal, this is the first place I think to go—I can chat with the bartenders and get a couple of drams alongside vibrant Oaxacan food.” —Julia Momose
Why we love it: Whether you’re huddled up inside with a fancy-pants cocktail or sunning yourself on the patio with a Miller High Life, it’s easy to see why Sportsman’s Club is such a beloved cornerstone of Chicago’s bar scene. The staff here operates as a unified force: They get along and have fun doing it, an attitude that permeates the room with positive feels. Maybe that’s why we always leave this place in a great mood.
From the panel: “You are not really in the Chicago restaurant scene unless you have spent Sundays in Sportman’s Club’s backyard, when the liquor and beer are flowing, a chef from one of your favorite restaurants is grilling and the Sportsman’s team is holding court behind the bar.” —Belinda Chang
Why we love it: If you run with winos, chances are you’ve seen this Bucktown bar pop up on your feed. If not, know that industry experts and neighborhood folk alike are raving about it. An extension of the wine shop by the same name, Red & White specializes in natural wines and elegant bar snacks, like the anchovy toast with goat cheese and preserved lemon. The best way to order? Grab a seat and let your knowledgeable bartender pick the right pour.
From the panel: “After being known as a great bottle shop, Red & White finally opened its bar. Serving small-family selections and curating a beautiful list, their dream has come to fruition, and we can all share in it.” —Ed Marszewski
Why we love it: When we need a break from the city’s repetitive cocktail lounges, we descend into the basement of Green Door Tavern to grab a drink at this secret speakeasy. Owner Liz Pearce has more than 100 funky cocktails that are described on custom tarot cards. Each night, the team selects a handful of cards from the deck, allowing for a wildly different experience with each visit.
From the panel: “Pearce’s tarot card cocktail menu is innovative and unique—a welcome injection of fun in a time when too many of our city’s cocktail menus are staid, copycat endeavors that can leave the modern drinker thirsty for a better option.” —Christopher Marty
Why we love it: When we heard that Jim Meehan and the folks behind Heisler Hospitality (Sportsman’s Club, Bad Hunter, Pub Royale) were hatching a Frank Lloyd Wright–inspired bar, we were skeptical. But when Prairie School opened in September 2017, the vision was clear: The dreamy space was marked with restrained nods to the legendary architect. Despite rave reviews and a strong industry following, Prairie School shuttered in May due to a lack of financial sustainability; Meehan says it was “the most ambitious bar [he’s] ever been a part of.”
From the panel: “Prairie School has a beautiful design that differs from any other bar in Chicago. It’s sleek but warm and pleasant.” —Caitlin Laman
Why we love it: Veggies are king at this West Loop darling, and that mentality carries over to the cocktail menu, too. Without going full green juice, the balanced beverages incorporate hints of jalapeño, carrot, rhubarb and other market produce. Looking for a harmonious pairing? Match the Spicy Carrot Cooler (white wine, carrot juice, Jamaican jerk bitters, pineapple, tequila and banana liqueur) with the Bad Hunter burger, a bean-based patty topped with cheddar, tomato jam, onion and mustard aioli.
From the panel: “There is a sort of understated magic about Bad Hunter. The team’s use of seasonal and fresh ingredients, which cross over between the kitchen and the bar, creates a cohesive experience that I will always cherish.” —Mattias Horseman
What’s in it: Gin, house-made fennel–calamansi (Filipino lemonade) tonic.
Why we love it: Served in a wineglass and garnished with whatever’s in season, this G&T is the kind of drink you want to be holding when you’re photographed on the bar’s breathtaking terrace.
What’s in it: 10-year Scotch whiskey, bourbon, vermouth, Grand Marnier and a whiskey float.
Why we love it: We can appreciate a cocktail that doubles—sorry—triples down on brown spirits. One sip of this stunner has us doing our best Ron Burgundy impression.