Baby, It's Cold Outside

Maya Silver |
Beer, Wine, and Spirits

You’re barreling down a frigid avenue, your head buried in your coat, as an assertive wind delivers a Lake Michigan chill to your cheeks. Desperately, you duck into a bar, emerge from your many layers, and breathe a warm sigh of relief. Welcome to one of Chicago’s coziest cocktail lounges! They say whiskey is the “sweater you wear inside,” but we believe liquors of all kinds are capable of warming from within.


Start by following your nose toward the powerful potpourri of cinnamon, vanilla, and orange flowing from Rebar {401 North Wabash Avenue; 312.588.8000}, located on the mezzanine level of the Trump Hotel Chicago. This is actually the scent of their Winter Magic—a housemade mulled wine, which you can sip while reveling in views of Lake Michigan, and relaxing amongst the serene scheme of deep purples and mahoganies. For a drink to match the wintry landscape, try the Snowtini—Godiva White Chocolate, Goldschläger, and black-cherry vodka.


Speaking of vodka, the bartenders at Potter’s {124 South Wabash Avenue; 312.917.3404} age Belvedere in oak barrels and then infuse it with vegetables, citrus, and peppercorns. This becomes the zesty nucleus of the house Bloody Mary, fortified to order with housemade mix, Guinness, and other lively additions. Potter’s sports a vintage feel with leather lounge furniture and Art Deco lighting that implore the enjoyment of a Manhattan with Potter’s signature Woodford Reserve Bourbon.


Continue to rage retro at Drumbar {201 East Delaware Place; 312.924.2531} where you’ll feel like an extra on the set of Mad Men with brown leather couches, bartenders donning old-school vests and bow ties, and throwback cocktails to match. To stay warm on a cold night, spice things up with the Mulled Wine—a bold glögg-esque drink of Malbec, Cognac, and seasonal spices—or the Yesterday’s Gone—rum, Sherry, cinnamon, lime, frothy egg white, and Aztec chocolate bitters.


There’s no egg, but plenty of nog in the Eggnog, one of the 45 martinis at the Redhead Piano Bar {16 West Ontario Street; 312.640.1000}, singing with spiced rum, Baileys, and nutmeg. Craving a sugar cookie or a slice of Key lime pie? Redhead’s got you covered with martini versions of those and many other treats, too. Fire off your wintry song requests to the piano man and sip away.


If you seek bonding time with your drinking mate—rather than entertainment—then visit Q2 {1625 Hinman Avenue; 847.570.8400}—a stately yet relaxing spot with pristine carpeting, white paneled walls, and comfortable lounge furniture. Instead of distracting TVs, Frank Sinatra croons as the fireplace crackles. The bartenders’s favorite seasonal sip? The Solstice—absinthe, gin, Lillet Blanc, Cointreau, and lemon juice, with a twist. Look forward to other cold-weather classics, too, like Hot Buttered Rum and a Fruitoddy.


Orchards may be on hiatus, but fruity cocktail fans can still Grow a Pear—a seasonal cocktail of gin, pear brandy, sage syrup, and ginger beer—at the The Boarding House {720 North Wells Street; 312.280.0720}, where the wine bar’s overhead light installation twinkles with 10,000 glasses. As you admire the wine-themed artwork, sample a glass from their vast selection, including everything from Grecian Whites to Alsatian Sensations spun from noble grapes. What better way to warm up than to travel vicariously to a Mediterranean island via your vino?


On the sparkly side of the grape, Pops for Champagne {601 North State Street; 312.266.7677} will make you feel like you’re inside a giant glass of bubbly, with decorative panels and mirrors of various shades, shapes, and sizes reflecting the lights of the city. Fulfill your winter spice craving with the Red Sky at Night—Calvados, dark rum, rosemary syrup, ginger beer, and Cava. For other sparkling cocktails, Pops uses natural true Champagne when it’s destined to be the featured flavor; Cava when other racier ingredients are at play; Prosecco for fruity concoctions; and sparkling rosé for Bellinis.


Beneath Pops is, as a guest once observed, “your rich uncle’s basement in Wisconsin.” Campy stone walls, a generous stroke of mustard yellow, and vintage armchairs make you feel right at home at Watershed {601 North State Street; 312.266.4932}. Put your feet up, envision a fire, and sip a hot cocktail featuring Great Lakes regional spirits—like the Campfire Cider, built with Seedling Farms Cider, apple brandy, peated whiskey, and thyme syrup for a smoky campfire kick.


While you’re sitting around the proverbial fire, consider a belated 2014 resolution to escape your cocktail rut. The Barrelhouse Flat {2624 North Lincoln Avenue; 773.857.0421} thinks outside the drink with idiosyncratic libations. Feeling chilly? Put on the House Sweater—Cocchi Barolo Chinato, Cocchi Torino, and other esoteric ingredients we promise will warm you up. And Whiskey Gingers are so 2013! Instead, sip the Monkey Biscuits—bourbon, Carpano Antica, Cynar, vanilla and cinnamon syrups, Angostura, a whole egg, and imperial stout.


For other novelties in warm, wintry beverages, visit Enso Sushi & Bar {1613 North Damen Avenue; 773.878.8998}, where bartenders infuse sake with cinnamon sticks and simple syrup—a warm, holiday twist on the Japanese classic. The Hot Cinnamon Sake stars alongside fresh apple cider and smoky whiskey in the Apple Blossom. In February, order your loved one a Bloody Valentine, featuring freshly-squeezed blood orange juice, vodka, thyme, and Napoleon Mandarin Cognac. Speaking of February 14, Enso Sushi & Bar is the perfect spot for a V-Day or wintry date amidst dim lighting, cozy leather seating, Mason jar glassware, and red votive candles on each table.