With all this highfalutin' boozing, I was hard-pressed to imagine a day when drinking wasn't legal here. But that doesn't mean it wasn't going on: During Prohibition, Chicago and a few other Great Lakes cities were distribution hubs for alcohol coming from Canada and U.S. moonshiners. Speak-easies and brothels flourished in the Levee District, near the South Side of Chicago. Some of them — the speak-easies, I mean — are still around. The history museum's historic bootleggers tours visit four Prohibition-era watering holes still in operation.
Some, like the Green Door Tavern, the Kerryman and Marge's Still, were known for their bathtub gin (which may or may not have been made in a bathtub). The Twin Anchors, a bar now known for its strict no-dancing policy, once operated as a speak-easy but disguised itself as a soda fountain. If you're tall, as I am, getting through the cubby-sized trap door that the Anchors' owners used to make a quick exit during raids is no small feat.
It's said the Anchors became the second home to Frank Sinatra, who was not shy about his love of drink or Chicago. He was also a regular at the Pump Room, which recently got a face-lift, courtesy of hotelier Ian Schrager. Sinatra's private table remains, as does the swinging vibe. The room is gently illuminated by hand-painted Italian light fixtures that resemble planets floating in the night sky. On Saturday nights, the Pump Room hosts a supper club where the hip crowd tosses back well-crafted drinks, including the Old English Gentleman, made with Dewar's White Label, tobacco syrup, fresh lemon sour, sweet vermouth and egg.
The Bedford in Wicker Park is another made-over joint. The converted Art Deco bank vault is home to some of the city's best cocktails and comforting vegetarian food. It also hosts an industry night on Mondays, when travelers can mingle with the city's restaurant staff. Chefs and bartenders are drawn by classic drinks and the presence of Fernet Branca on tap. This Italian liqueur, which is made with several herbs and spices, has a cult-like following, thanks to what's said to be its digestion-promoting properties and unique taste, which reminds me of bitter black licorice and Listerine warmed over a campfire.
Also popular among local industry insiders is Jeppson's Malört, a distinctively Chicagoan distillate made from wormwood, used in absinthe. Bartenders around town challenge themselves to make something potable with the firewater, which has the bite of citrus pith and the burn of bootlegged moonshine. Each time I revealed my out-of-town origins, bartenders tried to push the stuff on me. I'm now an unofficial Chicagoan.
One of the best iterations is the Wicker Park Sour at the Violet Hour, a hipster bar just off the Damen stop on the blue line. Here, Malört is combined with grapefruit, honey syrup, egg white and angostura bitters. A less toxic tipple on the menu — and one of my favorites of the trip — was the bourbon-based Woolworth Flip, whose frothy sarsaparilla notes come off as an adult root-beer float.
The Whistler is a quick cab ride from the Violet Hour, a low-key watering hole that also operates an indie record label, doubling as a venue for local musicians. The menu is small and the drinks are gimmick-free. The vibe at the Whistler is decidedly homey, like Echo Park minus the I-know-better-than-you attitude.
After trying the Elk's Own, a wintry mix of Old Heaven Bonded Bourbon, ruby port, Cynar, lemon, egg white and a walnut liqueur rinse, I can see why it has garnered so much attention. But here it's about hospitality, approachability and that quintessential Midwestern charm.
"It's always popular to be doing something honest," says Robert Brenner, a co-owner of the Whistler. "We are a city that's not content with mediocrity."