The Best Old Fashioneds in Chicago, According to Bar Pros

If you’re an Old Fashioned drinker, Chicago is your kind of town. The simple whiskey cocktail has deep roots in the Midwest, and it’s arguably the most popular order in the Windy City. “I’ve made more Old Fashioneds than any other drink in my life,” says Abe Vucekovich, beverage director at the Meadowlark and co-owner of Friends of Friends. 

Aneka Saxon, of Machine Hospitality Group, agrees. “[In Chicago,] you can trust a bartender to make an Old Fashioned, no matter what bar you’re in,” she says. “That’s not true in every city in every country. But in Chicago, I think it is true. And I think [that’s] why we lean on it so hard.”

Simple and strong, with spice notes from both the whiskey and bitters, the cocktail is balanced by a touch of syrup sweetness. The Old Fashioned’s simplicity makes it a cocktail that has nowhere to hide. By the time you’re nearing the end of the drink, “it opens up, and you get all the nuances of the flavor and the dilution has balanced out the sugar,” says Saxon. “It’s really cold, and it makes you want to go right back around for another one.”

Locals have strong opinions about where to find the best Old Fashioneds in Chicago, and local bar professionals even more so. Here are the places they go to drink a perfectly made Old Fashioned.

Hawksmoor: for British hospitality

Drinks at the Chicago branch of London’s Hawksmoor mean dark wood furnishings, old-world ambiance, and the promise of “Beef & Liberty,” as noted on the sign overhead. “When I’m not enjoying our Buttered Toast Old Fashioned at Broken Shaker, I love sipping on the Full-Fat Old Fashioned made with Michter’s Rye at the Hawksmoor,” says Judson Sherman-Rose, food and beverage director at Freehand Chicago. “It is fat-washed with a salted brown butter that adds a creaminess to balance the rye.”

Bamboo Room: for a tropical hideaway

The Bamboo Room, a cozy sidecar inside the popular tiki haven, Three Dots and a Dash, offers rum cocktails and a back bar of rare and vintage bottles. “A longtime favorite order of mine at Bamboo Room has been a Rum Old Fashioned,” says Dan Smith, general manager at Queen Mary Tavern. “I especially love a heavy pot-distilled St. Lucian rum. They’re hard to come by these days for some reason, but I know the good folks at Three Dots and Bamboo Room have a plentiful supply.” 

Lemon: for the new-school bar with old-school chops

“My go-to for Old Fashioneds in Chicago is definitely Lemon,” says Miranda Breedlove, director of beverage for Hyatt’s Lifestyle Group. “The drink is classic, straightforward, soul-warming, and brings up a bit of nostalgia, all of which they fully encompass. They know how to make all the classics particularly well and have the best hospitality that will make you feel right at home with this OG cocktail.”

At Lemon, you can order off a quirky menu of cleverly original cocktails, or look up at the chalkboard for a laundry list of thoroughly practiced versions of some unexpected classics. 

Queen Mary: for industry grogs, smoked whitefish dip, and saltines

Michael McAvena, cofounder of the Chicago-based liqueur company Wilderness Club, enjoys this neighborhood tavern for the classic whiskey cocktail. “One of my favorite bars for Old Fashioneds is Queen Mary,” he says. You might feel like you are aboard a sailing ship after a couple of drinks at this maritime-themed saloon in Ukrainian Village. “Every cocktail they execute, whether classic or signature, is of the highest quality. Sipped their Naval Strength Old Fashioned [split base of Hayman’s Gin and Smith & Cross Rum] the other night and it was fabulous.”

Best Intentions: for dive bar excellence

Best Intentions, in Chicago’s Logan Square, is a bartender favorite for solid cocktails, cheap and tasty smash burgers, and Angostura shots all around. “Best Intentions is hands down one of the best places to go for a classic cocktail,” says Vucekovich. “You can really trust that they are going to be making it, maybe not exactly the way you’ve had it before, but obsessively giving a fuck about a cocktail that some people would turn their nose up at.”

Billy Sunday: for a dose of amaro with vintage vibes

Dark, moody, yet comfortable enough for ripping shots of Malört, Billy Sunday has more amaro on the menu than anywhere else in town. “My favorite place to get an Old Fashioned would be Billy Sunday,” says Mason McIntire, managing partner at cocktail bar Lemon Chicago. “Not only is that where I learned to bartend, so I’m a little biased, but I really appreciate their take on it. Instead of the traditional bitters, they use an amaro, which adds a really nice complexity and depth to what is otherwise the most classic of cocktails. In fact, a lot of their classics are tweaked a little bit to make them a little more unique to that spot itself. So it’s kinda fun to see their take on all these beloved drinks.”

Small Bar: for corner bar vibes

For a neighborhood spot that still feels true to its Chicago roots, Small Bar is the place. Look for the Hamm’s sign on the corner of Albany and Wellington and grab a seat at the bar, or on the patio, if the weather is decent. “I like my Old Fashioneds simple and straightforward, [and] decidedly unfussy, so a cozy neighborhood spot like Small Bar is my go-to,” says Katie Renshaw, lead bartender at Hawksmoor. “Plus, their burger is a solid pairing for something strong and stirred.”

Kumiko: for high-level craft

“One bar that really impresses me is Kumiko,” says Jose Hernandez, lead bartender at Adalina Prime. “Everything there feels very intentional.” 

An evening at Kumiko is a lesson in Japanese hospitality and their refined cocktail culture. The menu is filled with thoughtful riffs on classics and seasonal originals.

“I love their highball menu, but their Old Fashioned is one I also can’t stop talking about,” says Hernandez. “It’s made with 20-year sherry and Mars Iwai Japanese whiskey, which makes it an approachable but refined way to get into these types of spirits.”

Bavette’s Bar & Boeuf: for timeless energy and a dry-aged rib eye

Bavette’s, in River North, is a standout in a sea of Chicago steakhouses that folks single out for their plush decor and outstanding bar program. 

“It’s about the build of the Old Fashioned cocktail — the correct shake of bitters, the rich Demerara sugar, the choice of whiskey (get the Russell’s Reserve 10-year bourbon), the ice — but the room and the ambiance complete the package and set Bavette’s apart,” Ryan Rezvani, bartender at Longroom and cofounder of Bitter Ex Bitters & Syrups. “If you’re on the main level, it’s sexy, romantic, lively, and jazzy, while the downstairs is dark, vintage, and classy.”

Big Star: for Wicker Park hangs with a turntable

The menu at Big Star is all about tacos and queso fundido, but the drinks are for booze lovers of all stripes, from powerful Margaritas to a stellar whiskey list. Robert Haynes, cofounder of Apologue Liqueurs and Hoste Cocktails, is a fan of the place for various reasons. “My go-to for an Old Fashioned has gotta be Big Star Wicker,” he says. “They’ve got a killer whiskey selection, great tunes, and the bar is a fun hang. I’m also perpetually hooked on their fish tacos.”