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From Grungy to Gorgeous: Chicago Spruces Up its Old Watering Holes

What happens when that bar down the street with a storied past gets new owners, a spit and polish, and an update to the drinks menu?

For a while there, the craft cocktail scene in Chicago was all about whatever was new. Guests would crowd into the high-concept, culinary-inspired Aviary in the Fulton Market District, or head over to Logan Square’s agave-focused Mezcaleria, or toast tipples at Michelin-starred GreenRiver in the well-heeled ‘hood of Streeterville.

Meanwhile, Chicago is dotted with old bars, ones that enjoyed quite the reputation a lifetime ago – maybe two lifetimes. If you ask the right bartender, they’ll tell you whether that reputation was swanky or salacious. There’s been a trend afoot in Chicago to reclaim its glorious boozy past, by applying a little elbow grease and wipe the grime off of spots that used to be something else. Some of them were neighbourhood dives, including ones that had been shuttered for decades. One was a scofflaw pharmacy that slung gin in defiance of Prohibition. Another was a factory that made ammunition (and bras) during the War. These are bars that – as one called the Sparrow says of itself – have been “rediscovered and reclaimed from the urban dust.”

The best way to hear the real stories behind these seven Chicago cocktail spots is to settle onto a bar stool with something long and strong and see what the bartender will tell you. Here’s what we can share until then.

The Berkshire Room/Bodega

Before it housed these progressive cocktail lounges, Acme Hotel existed as a shabby property known as the Berkshire Hotel. You know the type – the kind of place that usually serves as a last resort for travellers who waited too long to find accommodations. Its heyday was during the Roaring Twenties, and the owners of the bar have painstakingly incorporated some of the splendid materials from the original structure that went ignored for a long time. Beverage director Benjamin Schiller says it would have been too easy – and predictable  – for them to go with the same old speakeasy theme for the Berkshire Room when Acme Hotel reopened in 2012. Instead, the team incorporated the old with new elements like custom-designed lockers housing vintage spirits, giving it a fresh setting. Classic gin and whiskey cocktails, plus barrel-finished concoctions (cocktails aged in bourbon and wine barrels), dominate the menu.


15 E. Ohio St., 312-894-0945


Berkshire Room

Spilt Milk

One of the more popular ways to hide speakeasies in plain sight during Prohibition was to use a pharmacy as a cover. There were many throughout the country, and one that has been recently revived after more than 20 years out of commission was one in Logan Square. A few cool speakeasy tricks have been left intact, such as a secret passageway for an easy escape. Spilt Milk plays up the fact that many illegal taverns sold patrons tumblers filled with milk or soft drinks topped off with whiskey, gin or other spirits. Cocktails are composed in vintage stemware, and daily offerings feature clarified milk, freshly squeezed juices and pink lemonade. In a sense, Spilt Milk bartenders pay homage to those old-time pharmacy soda jerks by churning out pineapple soft serve, spiked with the cocktail of the day. 

2758 W. California Ave., 773-413-8440


There’s no other way around it: There were some shady goings-on in this West Loop venue long before the team behind MoneyGun took it over in 2016. Nondescript and unassuming, the bar boasted cheap drinks and scantily clad female servers who were rumoured to give lap dances to regulars during the 1990s. But that has all changed: The intimate (but not intimate in that way) space now attracts area residents rebelling against the over-the-top taverns and eateries in their midst. Much hasn’t changed regarding décor; MoneyGun has smartly spiffed up the interior with a few coats of paint and a little polish on the leather booths, but that’s it. While the drink menu boasts classic drinks considered ironically cool (think cuba libres and cosmos), imbibers will love the fact that they’re all $10.75.

660 W. Lake St., 312-600-0600


The California Clipper

When the Great Depression set in during the 1930s, many felt the need to throw back a few to escape reality. The California Clipper popped up during that era to accommodate the masses, and boy did it ever. After eight decades as a shot-and-a-beer saloon, the new owners have reinvented the Clipper as one of the hippest trips in Logan Square. The room, reopened in 2014, looks like a glossier version of its 1930s self, with craft cocktails replacing the former beer-and-bar-rail offerings. Roomy booths and antique sofas look comfortable enough to settle into for the evening, and near the entrance there’s a shrine to the Clipper’s past, incorporating original photos, stemware and other relics. The best part is that you can still count on live entertainment at least five nights a week from cabaret to experimental jazz.

1002 N. California Ave., 773-384-2547

Cherry Circle Room

Long before the Depression and Prohibition, wealthy Chicago guys were hobnobbing in what was once the exclusive, men’s-only Chicago Athletic Association. One of their favorite places to swap war stories was the Cherry Circle Room, which still serves some of the original menu items from the 1890s. The dimly lit room, hidden on the second level of what’s now known as the Chicago Athletic Association Hotel, feels like that secret date spot you want to keep to yourself. It’s stood the test of time, and so have the cold-smoked beef tartare, oysters and prime rib. Feel like showing off? Give a nod to the server, and he’ll send over the tableside cocktail cart equipped to make a manhattan, negroni or old fashioned to your fancy.

12 S. Michigan Ave. 312-792-3515

Cherry Circle / Courtesy Clayton Hauck

The Sixth

With an eclectic selection of restaurants, locally owned retail shops and more, the Lincoln Square neighbourhood has quietly positioned itself as a great place to check out. One of its standouts is The Sixth, a lounge with local bar star Benjamin Schiller behind the stick. His cocktails have caught the eye of every cocktail writer in town. Many are taken by the interactive “silly rabbit”: Guests are encouraged to tweak the drink to their liking using flavour-infused ice cubes. The history of the building is even more fun and fascinating: It dates to the mid-1880s, and during the Second World War it housed a factory staffed by Women Ordinance Workers. They produced ammunition for the war effort – as well as lingerie – up to the 1960s.

2200 W. Lawrence Ave., 773-433-5959 

The Sixth


Back in 1927, the Sparrow apartment building landed in the heart of the Gold Coast, angling to attract single young professionals as residents. Its Art Deco design, amicable doorman and lobby bar were also part of the draw, and the new owners have revived that vibe when reopening it in late 2015. Sparrow’s setting harks back to glamorous hotel lobby bars, complete with a vintage phone booth, whimsical wallpaper and low-slung antique sofas and chairs. Imbibers indulge in a host of 1930s-era rum focused cocktails, and shouldn’t feel silly ordering frou-frou drinks like the grasshopper, topped off with house-made rum cream.

12 W. Elm St., 312-725-0732

The Sparrow / Courtesy Nicholas James

Published Friday, January 27th 2017

Header image credit: MoneyGun



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