Three Drinks In: Chicago, Illinois

We got one of the top Windy City whiskey experts to reveal his three favorite drinks to order in his hometown.


Martin Duffy should be called the whiskey king of Chicago. A Windy City native, he’s worked in the booze business for more than a quarter-century, watching the local craft-cocktail revolution unfold before his eyes. For 14 years, Duffy served as master of whiskey for drinks conglomerate Diageo, representing dozens of brands including Johnnie Walker, Crown Royal, Bulleit, Bushmills, and George Dickel, and he later was a brand ambassador for whiskey friendly liqueurs Bénédictine and B&B. Today, he co-produces the Chicago edition of the Independent Spirits Expo and is the American brand rep for Glencairn, the Scottish company that produces those bell-shaped whiskey-nosing glasses that are ubiquitous at tastings around the world.

“When it comes to cocktails, I am not as adventurous as I once was,” Duffy admits. His favorite local drinks tend toward the simple, but where they are served encompasses the full range of Chicago’s thriving bar scene, from a hipster-friendly mixology spot to a classic tavern that has been around forever. Here are his current three favorite spots and what to enjoy at each.

Talisker Distiller’s Edition Scotch Whisky & Belhaven Wee Heavy Scotch Ale at Duke of Perth

Duffy calls this pairing simply “a nip and a pint,” but the particular ingredients are of crucial importance. “The spice and sweetness of this island single malt glides perfectly over the tongue and blends effortlessly in the mouth with a small sip of the creamy and slightly caramel ale,” he explains. Appropriately, the only place you can find both components is at the only Scottish pub in town. The Duke of Perth offers dozens of different single malt Scotches, along with a British Isles—heavy beer list and, of course, some over-the-top snacks, including mac-and-cheese fritters and all-you-can-eat fish and chips every Wednesday and Friday.

Sidecar at The Matchbox

This hole-in-the-wall has been in business for more than 75 years, but “started doing fresh juices and the finest ingredients in a no-fuss, no-muss style back in the mid-’90s and hasn’t changed a bit,” Duffy says. “It’s Chicago’s original cocktail bar.” A mix of cognac, orange liqueur and sugar, the Sidecar seems an odd choice for a whiskey guy like Duffy, but the old-school classic has been a favorite of his for years. “This cocktail is damn tasty on a hot summer’s eve,” he says.

Manhattan at Longman & Eagle

Located in the hipster haven of Logan Square, Longman & Eagle checks all the boxes for a cool restaurant these days: farm-to-table, nose-to-tail dishes and exquisitely crafted cocktails. There are even six rooms above the place you can rent for an evening, complete with vintage cassette players and mixtapes. But most importantly, the establishment is a whiskey palace, with a library of 300 bottles and a rotating assortment of spirits available for $3 a pour. “Though there are a slew of great whiskey bars in this town—Fountainhead, Delilah’s, Sable, Twisted Spoke, etc.—L&E has just always done a great job with whiskey cocktails,” Duffy says. They’ll make you a Manhattan however you like, but to have one Duffy’s way, order it on the rocks, with Punt e Mes vermouth and either Redemption Barrel Proof or Journeyman rye whiskey.

Check out our complete Three Drinks travel guide to cocktails