Spilt MilkAddress and Info
Matty Eggleston’s bartending career began in Los Angeles. Then, he took his California-cool cocktails -- that means seasonal produce, fresh juices, and vibrant flavors -- to Chicago to oversee beverage programs at Perennial Virant and Nico Osteria. Recently, he hung up his fancy pants to open a laid-back lounge on the corner of California and Fullerton. At Spilt Milk, he’ll welcome you with the house-infused vermouth shot of the day, followed by a craft beer or Sarsaparilla Zazerac (Old Forester bonded bourbon, sarsaparilla marsala, almond, and absinthe), thus proving you can take the bartender out of the fancy bar, but you can’t take the fancy out of this bartender.
Matt "Peaches" Frederick
EZ InnAddress and Info
Sometimes, a great bartender isn’t measured by the length of his beer list or how much mixology he shoves into his cocktails. Sometimes, he’s measured by how he makes you feel when you pull up a stool to that big, mahogany bar. You know, like that Cheers place. Except instead of Ted Danson, it’s Matt Frederick with a shot of whiskey, a can of Old Style, and a bag of potato chips at the recently rehabbed EZ Inn. The Aviary, Whistler, Bottlefork, and Cantina 1910 (RIP) alum found his way to Western Ave via a Craigslist ad. From there, it was a match made in fizzy, boozy heaven, with Frederick formulating, among other things, the bar’s popular draft cocktail program.
Bad HunterAddress and Info
Laura Kelton -- former Queen Mary and Bordel bartender, who started her bartending career in Chattanooga, Tennessee and recently took the reigns at Bad Hunter along with her gig at Sportsman's Club -- has a favorite saying when it comes to creating cocktails: “A cocktail should always be greater than the sum of its parts." Case in point, Mermaid Water (Dolin Blanc, Jack Rudy tonic syrup, gin, rhubarb, and Nardini Acqua du Cedro) is an iridescent pink cocktail that changes flavor as it sits, from a bright and citrusy to a more mellow rhubarb- and vermouth-forward drink. It’s garnished with a palm leaf that is shaped into a mermaid fin, because, according to Kelton, “Just because we are serious about cocktails doesn't mean we're not fun.”
Cindy’sAddress and Info
Spirit guide Nandini Khaund will take you on a journey with her mystical concoctions served at the rooftop bar of the Chicago Athletic Association. Set sail on the Aegean Sea (Plymouth gin, Salers Gentaine, dry vermouth, rhum agricole, Mugolio pine sap, and caper leaf) and followed by a stroll through the Grey Garden (vodka, Dolin Blanc, crème de violette, emperor’s jasmine pearl tea, and lemon). Just as the booze hits and the lines of Cindy’s arched glass ceiling begin to blur, remember We’ll Always Have Paris (Beefeater gin, Cocchi Americano, fresh strawberry, house-made pistachio milk, date syrup, cardamom, lemon, and rose petal).
BoleoAddress and Info
“The name comes from an expression often heard in my household after long working hours during peak times of brain fog, and because there’s cereal milk in it,” Jess Lambert says. She’s talking about Adulting is Hard (Dictador 12-year rum, Mistral Extra Anejo pisco, Lustau Oloroso pisco, chai-spiced cereal milk, and black lime), one of the many cocktails adding to the excitement of The Kimpton Gray Hotel’s rooftop restaurant and lounge. The Latin dance jams and beef heart skewers also help. Jess Lambert got her bartending start in Phoenix, but it wasn’t until she met Kimpton’s director of bars, Mike Ryan, who encouraged her to participate in the Tales of the Cocktail apprentice program, that she truly earned her stripes, currently at Boleo and Vol. 39.
Broken Shaker at the FreehandAddress and Info
Ain’t no party like a Broken Shaker party, and that party can’t start without the mezcal-loving Scotty LoBianco. A bit over a year ago, LoBianco traded in the buttoned-up, bourbon-soaked vibes of The Berkshire Room for the tropical oasis next door. The Chicago native hit his stride at the straight-out-of-South-Beach bar with cocktails such as Made that B!tch Famous (orchard fruit-infused Cognac, green apple parsley shrub, lemon, and hard cider) and Squash the Beet (reposado tequila, Ancho Reyes, Mexican spiced pumpkin, roasted beet, citrus, and spicy pepita salt) that take inspiration from Shaker’s equally impressive culinary offerings.
Pub RoyaleAddress and Info
“The Whiskey Cup (whiskey, Letherbee Royal Cup, lemon, and ginger) at Pub Royale represents everything I am as a cocktail creator,” says Kristina Magro. “It is a simple drink, nothing over-complicated, but flavorful and approachable to anyone who is a fan of whiskey.” And let’s be real, if you’re not a fan of whiskey, we’re not sure why you’re reading this. Before she found herself responsible for spiking your chai tea and dressing a hot sauce-covered Hamm’s, she could be found at Fulton Market Kitchen, Bordel, and Queen Mary. Recently, she also took up residence at the airy, agave-fueled Estereo.
GreenRiverAddress and Info
Find your way to the cocktail bar hidden on the 18th floor of a Streeterville medical building, and Julia Momose will be happy to make you a cocktail, shower you in Japanese whisky knowledge, or just turn that frown upside down with her dulcet voice. Seriously, the woman would make a killing if she got into the bedtime-storytelling business, but we’re glad she’s bartending. It means we get to enjoy her esoteric creations such as the MacSwiney (Pierre Ferrand 1840 Cognac, crème de noyaux, kirsch, vanilla, lemon, mascarpone cheese, and burlesque bitters) served in GreenRiver, or the Wink and Nod (Japanese whisky, amaretto, mastiha, and rice wine vinegar garnished with lotus root) currently on offer in Annex.
The SixthAddress and Info
One might say this guy has the coolest job in Chicago and that his skills are really sharp. Ice puns aside, Joel Rund is the mastermind behind the cubes at The Sixth. His program is responsible for freezing flowers in frozen blocks and capturing the flavors of Trix cereal in ice for the bar’s now-famous Silly Rabbit cocktail (gin, lime, and bitters served over grape, orange, lemon, and raspberry ice cubes). His comfort around a band saw -- The Sixth utilizes two Clinebell machines to freeze crystal-clear blocks of ice that are cut into custom cubes -- comes from a decade of carpentry work. His comfort behind the bar comes from even more time executing cocktail programs around Chicago, including Rebar and former Latin hotspot De La Costa.
Mezcaleria Las FloresAddress and Info
After years shaking palomas in Rick Bayless’ shadow, Jay Schroeder busted out on his own with a mezcal-filled cocktail bar in a former flower shop. At Mezcaleria Las Flores, he’s making drinkers fall in love with tequila all over again -- you know, because college left a mark. We’re not just talking about old faithfuls -- The Gringa margarita made with Corazon Blanco tequila -- but also more adventurous offerings, such as Sorry for Harambe (Mayalen Machetazo mezcal, figs, Guajillo chili, Bols Genever, lemon, and absinthe) that, according to Schroeder, “has definitely experienced a better fate than its namesake.”
1. Spilt Milk2758 W. Fullerton Ave., Chicago
2. EZ Inn921 N Western Ave, Chicago
3. Bad Hunter802 W Randolph St, Chicago
4. Sportsman's Club948 N Western Ave, Chicago
5. Cindy's12 S Michigan Ave, Chicago
6. Boleo122 W Monroe St, Chicago
7. Vol. 3939 S La Salle St, Chicago
8. Broken Shaker19 E Ohio St, Chicago
9. Pub Royale2049 W Division, Chicago
10. Estereo2450 N Milwaukee Ave, Chicago
11. GreenRiver259 E Erie St Fl 18, Chicago
12. Annex at GreenRiver259 E Erie St, Fl 18th, Chicago
13. The Sixth2200 W Lawrence Ave, Chicago
14. Mezcaleria Las Flores3149 W Logan Blvd, Chicago
Spilt Milk in Logan Square pays tribute to 20th-century Chicago taverns, both in its décor and its beverage program. The warm wooden tables and 40-foot mahogany bar are lightened by floral wallpaper and mint green tufted seat cushions throughout, and tin coffered ceiling tops the space. The drinks menu is decidedly austere; a selection of juleps, margaritas, sazeracs, and pisco sours puts Spilt Milk confidently above all gimmicks and frills, heightening its sense of sophistication. A mostly international wine list and six beers on tap are a worthy alternative for the cocktail-averse.
EZ Inn has been a staple Ukrainian Village tavern for decades, and with nearly 70 seats, there’s no shortage of eccentric folks who mosey in and out of the dim space. The bar’s 14 draft taps focus on beer from Chicago-based breweries, and boozy sodas are served as well as cocktails. Indie tunes fly out of the no-charge jukebox; it is a welcome addition to the throwback-themed space, which is complete with vintage license plates and retro beer advertisements.
This vegetable-centric concept from Heisler Hospitality (Pub Royale, Estero, Lone Wolf) has a rustic, outdoorsy aesthetic, complete with white-washed exposed brick walls, a communal bar-style table, and a smattering of potted plants along the walls. The spotlight is on locally sourced produce -- both fresh and wood-grilled -- but there are a handful of meat-based dishes as well.
Sportman's Club is dedicated to highlighting the best of lesser-known spirits, and to do that, it offers four different cocktails each day, whose ingredients are decided upon by whichever bartenders are manning the bar that night. What you drink one night probably won't be available the next, but that's what makes drinking here such a unique experience. Aside from cocktails, there's a well-curated selection of wine and beer, the latter of which includes Polish varieties that pay homage to the bar that formerly occupied the Ukrainian Village space.
Cindy’s is one of the most beautiful restaurants in the Loop with views of Millennium Park and Lake Michigan, but underneath its glass dome ceiling atop the Chicago Athletic Association Hotel it doesn’t simply rely on its looks. Cindy’s has a host of gifted bartenders who whip up unexpected “potions” like the Alsatian Rustbelt (made with Del Maguey Vida mezcal, Wolfberger Amer Fleur de Joie, lagunitas, and lime) that complement its upscale, seafood-forward menu. At brunch the egg dishes, like the cast iron-made quiche with chard, leeks, and gooey emmental, are buttery and light, and at dinner the shellfish platter and the grilled salmon with horseradish crème fraîche are both rich but pleasantly light ... but the late night fried cheese curds might be the sexiest thing on the menu.
Perched atop The Kimpton Gray Hotel, Boleo serves a peacock-colored menu that emphasizes South American, specifically Argentinian and Peruvian, flavors. The cocktail program is equally vibrant as the street food-inspired small plates menu, featuring tropical-flavored drinks like the pisco-based Chilcano with guava and strawberry. The rooftop lounge is sprawled across a 4,000-square-foot space, complete with a retractable, sun-filled, roof.
Vol. 39 is a highbrow cocktail lounge that serves a host of gourmet small plate options with all the sophisticated charm and dark wood accents of an old-fashioned study or smoking parlor where philosophy might be discussed over glasses of brandy. While it does offer an impressive number of brandies (and other fine spirits) on its extensive alcohol menu, it boasts a long, refined wine list and specializes in tried and true cocktails with top shelf twists like the Prescription Sazerac (made with rye whiskey, armagnac, barrel aged sugar, herbsaint, peychaud’s bitters, and lemon) and a variety of martinis. Vol. 39’s food menu matches its upscale cocktails with caviar, artisanal cheeses, charcuterie, oysters, and small plates like roasted bone marrow.
An outpost of the fabled Miami hotspot, The Broken Shaker in Chicago is located at the upscale hostel (yes, hostel), The Freehand. The bar has a laid-back house party vibe with vinyl-spinning DJs, back-to-back rounds of Jenga, and cozy couches. Bottle service is traded for punch service and unique cocktails like the Trailer Park Smash (bourbon topped with Miller High Life) color the menu.
This Anglo-Indian pub in Wicker Park serves Indian-inspired comfort food like salt cod samosas, palak paneer, and coconut curry mussels in an eclectic space decorated with taxidermy and colorful masks. The beer-driven menu features a well-curated mix of American IPAs, German Pilsners, and ciders -- both bottled and on tap. Though spicy, savory plates are the obvious choice at Pub Royale, don't overlook the chai dulce de leche doughnuts -- or the burger.
The guys from Heisler Hospitality (Sportsman's Club, Pub Royale) are behind this all-day corner bar in Logan Square. By day, Estero is a Modbar-equipped cafe serving Dark Matter coffee and pastries. At night, it turns into its raison d'être: an agave-focused cocktail bar. The triangular space is casual and bright thanks to garage door windows that open onto the street in the summer.
Between its stunning views of the city skyline and Lake Michigan, an Irish American-informed cocktail menu, and inventive dishes like white fish tartine with egg, radish, and celery, and sturgeon with bean ragout, turnip, and kale, there’s much to love about this swanky Streeterville spot. The space is streamlined, airy, and modern, boasting an attached terrace complete with plush seating prime for lounging over whiskey-infused cocktails.
Everybit the underground counterpart to its bright, 18th floor cousin GreenRiver, Annex is a small, swanky cocktail lounge with a limited seafood menu for people looking to indulge in something totally new. Along with head bartender Julia Momose’s favorite Japanese whiskey, Annex features a larger selection of spirits and surprising cocktails that you won’t find at GreenRiver or anywhere else. You can expect to find season and ingredient-inspired cocktails like Chorus Girls, made with Feni (Indian cashew liqueur), Italian herbal liqueur, Ambre vermouth, amchur (mango powder), turmeric, lemon, pineapple, and vanilla. The food menu includes options like seafood towers, artisanal cheese, and gin-cured gravlax. For the real VIP experience, Annex also offers champagne service … oh la la.
The team behind Roots Handmade Pizza runs The Sixth, a whimsical cocktail bar with out-of-this-world concoctions that will forever change how you see handcrafted drinks. Take the Game of Thrones-inspired Bracer, a rye-based cocktail served in an ox horn mug or the Spaceman Spiff, a mezcal drink served with a saucer that releases citrus and cedar smoke once removed. We told you, out of this world.
Connected to Johnny’s Grill, Mezcaleria Las Flores is Logan Square’s departure to Oaxaca via cocktail. Offering over 60 labels of mezcal, Jay Schroeder, a Rick Bayless alum, has created a bar program devoted almost entirely to agave. Besides testing your palate’s smoke tolerance with mezcal, you can enjoy other agave spirits like bacanora and raicilla. The cocktails -- all agave-based and served in ceramic mugs and other drinking vessels imported from Mexico -- range from crisp to smoky to adventurous. It’s a serious cocktail lounge without the pretention, blaring old-school hip hop and serving burgers from the grill next door.