Jacyara de Oliveira
of Sportsman’s Club
La Sirena Clandestina
During the year Oliveira spent living in Brazil during college, she often drank the country’s national cocktail, the caipirinha—a simple drink consisting of muddled limes, sugar, crushed ice, and cachaca, a liquor made from distilled sugarcane juice. Oliveira, whose family is Brazilian, also drank variations like the caipiroska (made with vodka) and caipirissima (made with rum).
La Sirena Clandestina has been one of her favorite places in Chicago since it opened in 2012, both for its Latin food and its mojitos, pisco sours, and contemporary Latin-inspired drinks. “It’s like walking into the kitchen of your best friend’s house,” she says. “It’s very close to what I would consider a perfect bar.” She was particularly impressed by bar manager Derek Payne’s caipirinha, a recipe that involves several forms of sugar, a special way of scoring the limes, and shaking the cocktail with chipped ice rather than crushed ice.
“Caipirinhas are great when you’re in Brazil—you’re typically sitting on a beach with the ocean at your feet,” Oliveira says. “But with a critical eye, they’re not necessarily the most delicious thing in the world. [Payne takes] a modern approach to building the cocktail. It’s a beautiful thing.” —Julia Thiel
For an equally excellent caipirinha, Oliveira heads to Bangers & Lace for bartender Cristiana DeLucca’s version. For a comparable South American feel, Oliveira recommends Argentine restaurants Folklore and ñ.
The Violet Hour
The old-fashioned is one of the oldest (ca. 1860s) and most basic of cocktails, which might make you wonder how a bartender could ever serve up a bad one, but McGee says he made plenty of them back in the 80s and 90s: “You would take a red maraschino cherry that had no flavor whatsoever and lots of red food coloring, stick it in a little bit of an orange half—we called it the flag. Then you’d open a bag of sugar and sprinkle it on top, muddle it to a pulp, and throw some kind of whiskey in there—it didn’t matter what—and splash it with club soda.”
After that, McGee says, the first old-fashioned he had at the Violet Hour was a revelation. “Just sugar, whiskey, bitters, and orange peel, served in a really nice glass with a big piece of hand-carved ice that makes it slowly dilute over time. That was a wake-up call for me for how that drink should be made well, so it’ll always have a special place for me. And they have a special bottling of Wild Turkey Kentucky Spirit that you can choose for it that’s barrel-aged and really spicy, so it holds up to the sugar and bitters. It has a nice backbone for the drink.” —Michael Gebert
McGee also recommends Benjamin Schiller’s old-fashioned at the Berkshire Room—”He’s got some really rare stuff, older stock you can’t find everywhere”—and the one at Billy Sunday: “They put a sugar cube and a little bit of amaro at the bottom, which acts as the bitters.”
of the Hopleaf
Metropolitan Dynamo Copper Lager
The Long Room
“Mighty Slim” isn’t the name on this beloved bartender’s W-2, but that’s what folks have called him for more than three decades—even longer than his 21-year tenure at Hopleaf. “The owner had to ask me my real name after I’d been working there three years,” he says. When he first introduced himself to me (I’ve been visiting the Hopleaf since 1996), he explained, “It’s like ‘Slime’ without the e.”
Slim’s favorite bar in town (disqualifying anywhere he works) is the Long Room. “The draft list always has trippy descriptions of what’s on tap. Good bartenders and good music,” he says. “There’s nothing like being there as the sun is setting in the summertime—the place just seems to glow. If they have the Metropolitan Dynamo Copper Lager on tap, all is well in the universe.”
Dynamo is available all year throughout Chicago, often on draft, and like all of Metropolitan’s beers (I especially love their doppelbock, Generator, a seasonal offering now being succeeded by Iron Works altbier) it’s a testimony to the bounty of the city’s craft beer scene. There aren’t too many places where it’d be so easy to take for granted a beer as good as Dynamo—or a bar as good as the Long Room. —Philip Montoro
of the Promontory
The Scorpion Bowl
Three Dots and a Dash
Hyde Park’s Promontory is hardly a tiki joint, but Sanders is no stranger to tropical drinks. Her signature cocktail is the Caribbean Cure, an island-worthy drink fueled by vodka, John D. Taylor’s Velvet Falernum liqueur, pineapple and lemon juices, and more.
When Sanders wants a getaway in a glass, she goes for Three Dots and a Dash‘s potent Scorpion Bowl, a substantial vessel of gin, brandy, and curacao, with hints of lime and orgeat, that serves up to five people.
“It’s made up of things that I wouldn’t usually drink,” she says, “which makes it that much more appealing to me.” And the flaming ship in which the drink is sometimes served gives it a “sailing-through-murky-waters feel,” Sanders says. “It’s super cool to look at and drink!” —Luca Cimarusti
For an equivalent equatorial vibe, Sanders recommends “the original time warp,” Hala Kahiki.
of the Drifter
Rhum agricole daiquiri
Sable Kitchen & Bar
A typical daiquiri is made with rum, lime juice, and sugar (often in the form of simple syrup), but Sable‘s off-menu variation of the classic drink substitutes rhum agricole, which is made from sugarcane juice rather than molasses. A bartender suggested the cocktail to Pearce when she was preparing for a trip to Martinique, where most rhum agricole comes from, and she’s been drinking it ever since. The substitution, she says, gives the drink a grassy, mineral flavor that’s distinct from the vanilla and maple flavors typical of regular rum.
And Sable is the most comfortable bar Pearce can think of—”any time of the day or night, for any occasion.” In her opinion, the food is amazing, the staff is knowledgeable, and the cocktail and whiskey lists are among the best in the country. “The fact that they aren’t open during the afternoon anymore is tragic,” she says. “It used to be my ‘office.’ I would just belly up with my laptop and sip my way to the weekend.” —Julia Thiel
of the Betty
For a decade, Peter Vestinos has happily been one of the regulars packed like sardines into the Matchbox, which at 460 square feet is famously a shoo-in for Chicago’s smallest bar. What initially drew him was the diminutive River West bar’s reputation for first-rate classic cocktails—one it’s maintained for 20 years—but these days his usual isn’t a mixed drink at all. Vestinos keeps things simple with a combo bar manager Colleen Bush dubbed the Rose’Ocho (the bar’s spelling): a glass of Ocho plata tequila with a rosé wine back.
“It’s the elevation of a tequila shot,” he says, in reference to the practice of biting a wedge of lime to cut the liquor’s burn. Another precursor: the Mexican tradition of chasing tequila with sangrita, a fruit-juice mix with chile powder.
“The tequila is on the sweeter side, and the rosé is more acidic,” Vestinos says of the Rose’Ocho. “So by doing a little rosé on the back, it brightens the experience of the tequila—and cleanses the palate.” —Jake Malooley
For Ocho tequila with a sparkling rosé champagne back, Vestinos heads to Pops for Champagne.