Chicago’s history with booze is as rocky as the ice in a well-made Old-Fashioned.
During Prohibition Chicago supported approximately 20,000 speakeasies under Mayor William Hale Thompson. Nicknamed “Big Bill,” Thompson was infamous for turning a blind eye toward Al Capone and his circle of booze-hoarding mobsters, and supported a police force largely involved in the bootleg business. Ironically, Chicago was also ground-zero for Prohibition: The 18th Amendment passed largely due to the staunch efforts of the Women’s Christian Temperance Union, founded by Evanston suffragist Frances Willard.
The city’s relationship with booze (and women—who have been permitted to be bartenders only since 1970) has come a long way since. Most of those 20,000 backroom saloons have long since shuttered, but a half-dozen century-old taverns are still packed until the wee hours, thanks to the city’s smattering of grandfathered 4 a.m. licenses. Wine bars—while less common than traditional taverns and dive bars—thrive with regulars. And thanks to the influx of new talent both on the sommelier and importer/distributor side, Chicago is carving out a diverse wine scene finally on its way to rivaling more famous American wine cities. On the cocktail front, Chicago is a city mature enough to embrace classic old-school Martini lounges alongside molecular-gastronomic hotspots.
As for beer, drinking it never went out of style, and making it is back en vogue. After lagging in the craft beer game, there are suddenly a half-dozen new microbreweries that call the city home, along with beer-centric bars supporting local brews and rarities. Craft distilleries are popping up faster than Vendome can weld stills, many of them with swanky bars attached.
And while it’s not news, it should be known: Chicago even has its own (unofficial) spirit in Malört, an anise-flavored, mouth puckering liqueur brought to the city by a Swedish immigrant in the early-20th century. It’s caused quite a stir over the past few years (cease-and-desists and lawsuits galore), and in response to the bah-humbug ex-Chicago brand that launched its infamy, several local bars have bottled their own improvements to the notoriously bitter spirit. —Lauren Viera