Chicago, My Kind of (Whisky) Town

Chicago has a long-standing reputation for being a great place to eat and drink. While that used to mean highly acclaimed dining at one place and expert mixologists slinging cocktails at another, today the line between fine dining and fine drinking has been blurred. Now there are venues that combine elevated cuisine alongside curated spirits selections and creative cocktails. And with its thriving craft distillery scene, Chicago makes a great destination for a whisky weekend.

The city is big but compact, so use the train system (known to Chicagoans as the “L”) and rideshares to see all of it.

Day 1

In the Windy City there are plenty of hotels with good bars, so you might as well stay where there’s a whisky focus. Hotel Zachary, across from Wrigley Field, provides views of the iconic baseball stadium and easy access to Mordecai, where creative takes on American classics like wagyu tartare and crackerjack beignets accompany an impressive whiskey selection of rare gems like a 24 year old Willett Single Barrel and vintage bottles dating back to the 1940s, like 1949 Old Overholt Bottled in Bond.

For a downtown option near the Loop, Chicago’s central business district, try the Acme Hotel for The Berkshire Room, a cozy cocktail bar with an excellent selection of American and scotch whiskies. The Bartenders’ Choice cocktail reads like a choose-your-own adventure, letting you pick the spirit, the strength, and even the glassware. The Nutella-washed E.H. Taylor Small Batch bourbon makes for a perfect sweet treat.

Start your exploration of Chicago with an Architecture Boat Tour down the Chicago River in the heart of downtown. It’s the best way to get your bearings, and it disembarks near several lunch options. There’s Sushi-san for outstanding sushi and more than 180 expressions of Japanese whisky, or Bub City for house-smoked barbecue alongside nearly 280 American whiskeys, including the 2023 Buffalo Trace Antique Collection, plus 18 private single barrels. For a laid-back vibe, Twisted Spoke serves satisfying comfort food from burgers to gumbo and hundreds of whiskies (heavy emphasis on American and scotch).

Walk off lunch with a trek to Warehouse Liquors in the Loop. Owner Gene Charness, a Keeper of the Quaich, is renowned for his expertise and impressive palate—proof of which are in his single barrel selections, from Laphroaig to Stagg and dozens in between. Binny’s Beverage Depot, which boasts one of the largest liquor selections in the country, is another option for purchasing souvenir bottles, with locations throughout the city.

For dinner, an absolute must is The Franklin Room. Every dish on the menu is delicious (especially the Chilean sea bass with sweet miso and morels) and its expansive selection of almost 350 whiskies, ranging from Redbreast 21 year old to Yamazaki Peated 2022 Edition. Not every whisky is listed on the menu, so talk to the bartenders or glance around the room before ordering. While some bottles lining the restaurant walls are the private bottle keep for guests, many overflow from the backbar.

End the evening at Delilah’s, one of the best whisky bars in the world. The unpretentious dive bar vibe contrasts with the unparalleled selection of more than a thousand bottles, a good reminder that whisky doesn’t need to be enjoyed in a fancy glass or wood-paneled setting.

Day 2

Start the day with brisket hash at Dove’s Luncheonette, a ’70s-style diner spinning classic vinyl. Or go with the bangers and hash scramble—scrambled eggs, sausage, leeks, potato, and cheddar cheese—at The Green Post. Stick around late enough to try their eclectic whisky selection, like Ardbeg Perpetuum, Middleton Very Rare 2016, or Old Forester Birthday Bourbon 2012.

Take the afternoon to visit The Art Institute of Chicago, see beluga whales at the Shedd Aquarium, or visit a distillery. Take the L’s Brown line to Koval Distillery, one of the country’s first craft distilleries, where Austrian distilling techniques are combined with unique barrel maturation (like amburana wood and maple syrup), for an interesting spin on their whiskey, all of which are bottled as single barrels.

Or take a rideshare to Judson & Moore Distillery for a flight of its bourbon, rye, red corn bourbon, and single malt. Tours are basic, but include the hybrid still and barrel aging room. The whiskey is fantastic, but what you’ll talk about later are the cocktails. Thanks to an archaic law restricting distillery bars to using only spirits made on-site, all of their cocktails are whiskey-based—including the Margarita (made with single malt) and Espresso Martini (with their bar-exclusive The Generator, a malt whiskey distilled from Metropolitan Brewery’s Double Bock beer and aged in single malt casks).

Another option is Maplewood Brewery & Distillery, making oat whiskey distilled from floor-malted brewers’ barley and a single malt inspired by their oatmeal milk stout.

If lunch calls for a beer break, rideshare to Forbidden Root in West Town, a brewery in a former movie theater offering upscale gastropub-inspired dishes like duck confit with ricotta gnocchi, paired with an Old Elk and Wild Turkey bourbon barrel-aged imperial stout. Or if it’s a weekend, head to Mrs. Murphy & Son’s Irish Bistro for classic Irish fare and more than 75 Irish whiskeys, organized on the menu by style for easy comparison.

Later, jump on the Blue Line to the Logan Square neighborhood, a trendy area dense with bars and restaurants. You can’t go wrong with Union, serving elevated Midwestern fare (think a wood-grilled pork chop with anchovy jus), next to a diverse selection of whisky (almost 100 bourbons, 50 ryes, and 80 world whiskies), and a revolving list of regional beers on tap. Try the flight of wheated bourbons (Weller Special Reserve, Larceny Small Batch, and Journeyman Corsets, Whips & Whiskey, $20) or a pour of the Fukano Chizuru Women Who Whiskey Release ($15). Pro tip: Their sticky toffee pudding pairs perfectly with WhistlePig 12 year Old World wine cask-finished rye.

Then finish up nearby at a longtime staple known for its food as much as its whisky, Longman & Eagle. They’ve been open since 2010, a testament to their inventive cuisine and extensive whisky list that focuses primarily on American, with around 500 bottles. Start with the bone marrow with strawberry balsamic bacon marmalade (don’t forget to add the whiskey luge) and finish with the French fry ice cream (malted chocolate mousse and Magic Shell, like your childhood fast-food dessert with fries) served with Corsair Dark rye. Order a pour of the L&E private barrel of High West Cognac-finished Double Rye and toast to a great weekend in the Windy City.