Owner Mike Miller behind the bar at Delilah's—a place not to be missed by any whisky fan, offering more than 1,000 whiskies from 15 countries.
Considering Chicago’s historical ties to notorious bootlegging mobsters, perhaps it’s not surprising that today the city has quite a robust—and nowadays legal—distilling scene. There’s plenty to explore throughout the city, especially for whisky lovers.
Koval Distillery was the first to open after Prohibition—in 2008—and offers a line of single barrel whiskeys, including bourbon, rye, four grain (oat, malted barley, rye, and wheat), millet, and oat; Chicago Distilling Co. and Judson and Moore Distillery both offer bourbons, ryes, and American single malts; Maplewood Brewery & Distillery makes single malts and ryes; Wolf Point Distilling makes bourbon and rye; and although CH Distillery specializes in vodka, it’s also home to Jeppson’s bourbon, plus Jeppson’s Malört, a traditional wormwood-based digestif that has achieved cult status with Chicagoans. And just outside the city, there’s FEW Spirits in Evanston, Quincy Street Distillery in Riverside, and North Shore Distillery in Green Oaks—all of them touting a plethora of whiskeys.
Touring and tasting your way through Chicago’s distilleries would certainly be a rewarding way to spend a visit, but the city’s bar scene is equally strong, with several venues boasting massive whisky collections that attract connoisseurs from far and wide. So next time you’re in the Windy City, don’t miss these five whisky-centric bars. Ranging from low-key neighborhood dives to upscale lounge experiences, there’s something here for every type of whisky drinker.
The Berkshire Room
This craft cocktail lounge at the Acme Hotel in River North offers more than 200 whiskies from around the world, many of which are allocated, limited releases, single barrel picks unique to the venue, or “dusties” (vintage or discontinued labels). Notable pours include an Old Fitzgerald from 1951 ($400/1 oz.), several vintage Old Grand-Dad bottles ($11-$62/2 oz.), the full Pappy Van Winkle line ($150-$250), a Berkshire Room single barrel pick of Weller Full Proof bourbon ($20), several versions of Bruichladdich Black Art ($149-$155), and Dalmore 35 year ($760).
“Our bar is over a decade old, and we’ve remained one of Chicago’s premier whisky bars,” notes bar manager Jesse Sexton. The Berkshire Room also has an outstanding cocktail program, with a list that includes the Free Bird Sour ($28), a Whiskey Sour made with a single barrel pick of Wild Turkey. There’s also a Van Winkle Old Fashioned, featuring the guest’s choice of either Van Winkle 12 year ($50) or Pappy 15 year ($150), as well as the “Dealer’s Choice” option, where guests choose a spirit, flavor profile, and glassware and the bartender takes it from there.
theberkshireroom.com
Big Star
While this Wicker Park taco joint has an impressive list of tequila and mezcal, it’s also well known for its expansive whisky selection. There are 145 whiskies to choose from, including many “rarities and specials,” including house-selected single barrels—the Blanton’s #20 House Barrel ($11/1 oz., $22/2 oz.) and Weller Full Proof Big Star #24 ($10; $20) are two of beverage director Laurent Schroeder-Lebec’s current favorites. “We also consistently carry the Buffalo Trace Antique Collection lineup ($21-$25; $42-$50), and I’m proud to say we can keep the Pappy line ($12-$52; $24-$104) in stock year-round,” he says. “One of my other favorites that people sleep on is Wild Turkey Kentucky Spirit ($20), and we always try to have that around.”
Slinging tacos, agave spirits, and whisky, Big Star has a honky-tonk vibe, with music being a huge part of their brand and employees spinning vinyl behind the bar. “Years back, you may have heard a lot of Bob Wills and Drive-By Truckers at Big Star, nestled among the best Loretta Lynn records; today you’re as likely to hear Dwight Twilley, Tom Waits, Bo Diddley, the Flamin’ Groovies, Sturgill Simpson, and much more,” Laurent says. “But our focus is the timeless tapestry of Americana, as it weaves together country, soul, rhythm and blues, folk, garage rock, some punk, and plenty of rock’n’roll.”
bigstarchicago.com
Delilah’s
This Lincoln Park bar is a must-visit destination for any whisky fan, with just over 1,000 whiskies from 15 countries on offer. This includes roughly 450 American whiskeys, 430 different scotches from over 70 distilleries and covering every region and style, and 130 from Ireland, Japan, Taiwan, Australia, Canada, India, France, Finland, Spain, the U.K., New Zealand, and more.
Delilah’s also has 20 of its own bottlings of bourbon, rye, and scotch that are only available at the bar, and for its 20th anniversary in 2013 the venue launched a collaborative whisky with Compass Box Whisky, aptly named Delilah’s, that’s now available internationally. Other notable menu highlights include Glenfarclas 40 year distilled in 1965 ($95/1 oz.), Knappogue Castle 1951 ($150), Longmorn Single Cask 31 year distilled in 1972 ($75), Macallan 36 year distilled in 1969 ($125), Springbank 39 year distilled in 1965 ($150), and Teeling 24 year old ($65).
Mike Miller, a renowned figure in the whisky world, founded Delilah’s in 1993 and the place quickly became a Chicago institution. It’s also popular for its music, which features DJs spinning punk, rock, metal, ska, country, soul, R&B, garage, and new wave nightly, as well as art openings, film screenings, and a host of beer, wine, whisky, and other spirits tastings.
delilahschicago.com
Longman & Eagle
This Logan Square spot is a contemporary take on taverns and public houses of yore. The first floor features the main space of the restaurant and bar, where diners can enjoy gastropub fare, craft cocktails, plus over 875 different whiskies, with a strong focus on American labels, including such prized pours as the Old Fashioned Copper Vintage 1990 ($250/ 1.25 oz.; $400/2 oz.), The Last Drop No. 28 ($500; $800), Old Crow Traveler’s Flask circa 1968 ($64; $100), and Double Eagle Very Rare 2019 ($250; $400). More than a dozen whisky-based cocktails are on its menu, including the Buck Ozug ($12), featuring Very Old Barton bourbon, lime juice, Gosling’s ginger beer, and Letherbee fernet, and a Manhattan ($32), comprising Longman & Eagle’s 2021 single barrel pick of Russell’s Reserve, plus Punt e Mes, and aromatic bitters.
Also on the first floor of the space is a backroom for more formal private dining, plus special events, and the Off Site Bar, or “The OSB,” which is a micro-bar located adjacent to the rear of the building, accessible through the main entrance or from the street. Finally, on the second floor is an inn with six guest rooms. “‘Eat, Sleep, Whiskey’ is our slogan, and it’s actually extremely literal,” notes bar manager Jay Cullen. “We give each of the guests at our inn two whisky tokens that can be redeemed for any pour from the ‘Whiskey for Drinking’ section of the menu.
longmanandeagle.com
Untitled Supper Club
This Prohibition-era-inspired, 18,000-square-foot venue in River North combines elements of a classic speakeasy, a contemporary lounge, and a high-end restaurant, with an impressive list of approximately 700 rotating whiskies to boot. “You can expect to find an extensive and diverse range of labels from around the world, including renowned single malt scotches, American whiskeys, Irish whiskeys, Japanese expressions, and more,” says bartender Krys Irizarry. “The bar staff is knowledgeable and passionate about whisky, and the menu caters to both novice enthusiasts and seasoned aficionados.”
Menu highlights include private barrel offerings of Blanton’s Single Barrel bourbon ($37/1.5 oz.); Stranahan’s American single malt ($19), Journeyman Last Feather rye ($15), Woodford Reserve bourbon ($15), and Knob Creek Single Barrel rye ($16) and Single Barrel bourbon ($16), plus “rare and limited” selections like Jefferson’s Reserve Marian McLain bourbon ($70), Heaven’s Door Bootleg Volume 4 bourbon ($110), Ardbeg 25 year ($140), and Macallan 25 year ($424) and 30 year ($600).
“Untitled Supper Club is also renowned for its entertainment offerings,” Irizarry adds. “Live performances, ranging from jazz and blues to cabaret and burlesque, grace the stage, providing an immersive and captivating experience for guests. The performances complement the overall ambiance, transporting patrons to a world of glamour and artistic expression.”
untitledsupperclub.com
