In partnership with Pinhook Bourbon
Though it’s one of the biggest cities in the world, Chicago is best understood and experienced as a network of neighborhoods. Officially, there are 178 of them, each with its own distinct personality and vibe — and at least one dependable community watering hole. There’s an argument to be made that Chicago, more so than any other city in the world, has perfected the neighborhood tavern experience. If the particular experience you’re after involves an expertly curated list of bourbons on offer, look no further than these six bars, all of them cherished by locals, celebrated by passers-through and united by their love and respect for America’s spirit.
We’re serious fans of a certain Chicago-set show about the trials, tribulations and evolution of a local sandwich joint, so that might be coloring this selection just a tad. But make no mistake: Jerry’s Sandwiches is a must-visit whether or not you’ve spent the last few months punctuating all your sentences with “Yes, chef.” At a joint named after Jerry Garcia, the so-called “cosmic” sandwiches take center stage, but the bourbon selection is incredibly impressive as well. Bourbon aficionados and newcomers will all find something here. We recommend Jerry’s Old Fashioned, made with Pinhook Rye, paired with the Marky B skirt steak sandwich.
4739 N. Lincoln Avenue
This jewel of the East Lakeview neighborhood serves locally sourced, Italian-inspired seasonal plates alongside an impressive bourbon selection. With a glass of Pinhook Bourbon in hand, you can savor a fusion of flavors cooked with respect to the history of Italian cuisine and the Midwestern farmers that provide the ingredients. Appropriately, the bar opens at 5 p.m. daily.
3124 N Broadway Ave
“Coffee, toast, whiskey and craft beer” doesn’t sound like a combination that should work, but Slightly Toasted has cracked the code and we’re very much here for it. The all-day bar and coffee shop houses one of Chicago’s largest whiskey collections, with more than 500 selections, 30 private barrels and 100 vintage and rare bottles. The atmosphere is cozy, the bartenders are seasoned and the team shakes things up with fun events like half-off whiskey Wednesdays and invite-only bottle and barrel shares where they crack open new, limited or rare releases.
22 N Clinton
The Hideout is the stuff of Chicagoland legend. The balloon-frame house, which was built in just two days over a century ago, was run by undocumented bootleggers and given its name by an unknown source when it legally opened in 1934, still has no sign on the outside (nor inside for that matter), and has for decades hosted musical performances from the obscure to the iconic. Despite its name, this gem isn’t exactly hidden. But it is treasured by the locals who fill it with a distinctively “insiders-only” vibe and contribute to the character and authenticity that make it the perfect spot for any bourbon enthusiasts to tuck in and savor a glass.
1354 West Wabansia Ave.
Delilah’s is a Chicago institution and a haven for anyone seeking a genuine dive bar experience. If you’re a fan of whiskey or beer (boilermaker, anyone?), you’ll be blown away by their massive selection. But if a menu boasting over 300 beers and 800 whiskeys isn’t enough to impress you, the vibes should do the trick. The bar is home to arcade games, film screenings, live music and art openings, and the jukebox is always spinning a killer mix of punk, garage, metal and alt-country.
2771 N Lincoln Ave
The neighborhood tavern meets a modern speakeasy at The Franklin Room. Here, elevated takes on classic American pub fare are paired with a highly creative, meticulously curated beverage program focused on limited releases and independent distillers like Pinhook. Make like a local and befriend the highly knowledgeable bartenders to get a perfect recommendation based on your palate and preferences. For true connoisseurs, Franklin Room’s Whiskey Keep program offers members access to an exclusive, by-the-bottle spirits menu; your purchase is kept in a secure cabinet until you’re ready to stop in and enjoy it.
The Franklin Room
675 N Franklin St.
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