8 of the best-kept secrets in the Chicago cocktail scene

By Nicole Bruce

Chicago’s craft cocktail scene is among the country’s best. And in a city where high-profile cocktail bars earn much of the spotlight, not all establishments slinging seriously impressive drinks get all the praise they deserve. Here are eight under-the-radar cocktail bars around the city that in-the-know locals have been keeping all to themselves.

The Sixth
Fifty/50 Restaurant Group's upscale yet laid-back bar is typically filled with eager drinkers—neighborhood locals grabbing a post-work drink and outsiders seeking a well-crafted cocktail—yet it's still an underrated spot. The fact is beverage director Benjamin Schiller’s inventive drinks are showstoppers. Channel warm rays with the Cruel Summer, a mezcal, hazelnut orgeat (like liquid marzipan), and pineapple concoction, or sip on the She’s Good to You, a Bourbon, brandy, coriander, strawberry, and rooibos tea creation garnished with a toasted cinnamon stick. Bar snacks like duck-fat frites and Bourbon-bacon truffles round out the experience.
Neighborhood: Lincoln Square MAP

Larry's
Helmed by the owners of coffee/bike shop Heritage Bicycles, this throwback cocktail lounge inside Uptown's renovated historic Lawrence House feels like a hidden gem—it's like a hotel bar in an apartment building, and there's no street signage. The low-lit space is tiny, but patrons can take their drinks into the building's more spacious lobby, a lounge/library/old-timey train station hybrid with a stained-glass ceiling, chandeliers, and armchairs. Greg Fleming curated a signature cocktail menu that doesn't stray far from the classics: a vodka and soda deemed Lady Louise adds Chareau aloe liqueur and lime cordial. But there's still room for experimenting, too—the house cocktail, Larry's, is a twist on an old-fashioned with salted coffee flavor and Elijah Craig Bourbon—a nod to Heritage.
Neighborhood: Uptown MAP

Ward Eight
It's just outside city limits, but the trek to Evanston's seriously underrated artisanal cocktail bar in the once-dry home of the Women's Christian Temperance Union is well worth it. A plethora of seasonally rotating, expertly crafted cocktails—often accented with whiskey-soaked cherries and hand-carved ice balls—range from $8 to $12. A delicious small-plates menu, and nightly themes like Monday Night Blues with live blues music (sans cover charge), Tiki Tuesday with rum-infused Shrunken Skulls, and Ward Eight Wednesday with $8 cocktails all night long, make it a vibrant social scene.
Neighborhood: Evanston MAP

The Motel Bar
For cocktails with a good story behind them, look no further than this retro hotel lounge–inspired bar in the old Montgomery Ward catalog building. Feed the jukebox, linger over late-night bites, and throwback tipples in circular, mod orange vinyl booths inside, or mingle out on the patio. An extensive list of reasonably priced classic cocktails—from martinis to Manhattans to Tom Collinses to Rob Roys—come in at the $10 price point. The five-page room service–themed menu also features snacks; think fried onion rings, petite grilled American cheese sandwiches with tomato soup, and assorted flatbreads.
Neighborhood: River North MAP

Paladar Cuban Restaurant & Rum Bar
Housed in a cozy, old brownstone with an outdoor patio, this neighborhood Cuban spot is a solid pick for authentic food and great drinks, plus live Latin music if you happen to come in on a Tuesday night. A cool rum bar in the back of the restaurant, Havana Club, offers patrons more than 60 varieties of boutique rums, where you can sip on the world's finest rums with a tasting flight or opt for one of the many specialty cocktails. Experience the golden days of Cuba with made-from-scratch cucumber and guava mojitos with fresh sugar cane juice, fresh fruit-topped sangria, or the Hemingway Special with lime and grapefruit juice, grenadine, and Boltran rum.
Neighborhood: Bucktown MAP

The Winchester
This Ukrainian Village staple might be best known for its brunch and dinner menus, but its revolving cocktail roster—dreamed up by renowned Chicago craft cocktail pioneer Reilly Drew—shouldn't be overlooked. Seasonal ingredients take center stage here: Lost in the Garden is a refreshing combo of peppery gin and bubbly brut with hints of rose and cucumber, while the Smoke Signal is the smoky rhubarb-strawberry cousin to the margarita. Then there's the quirky Rocket Highball, a rye whiskey highball with added complexity from dark chocolate, arugula, and coffee notes. It'll be hard to choose, but we don't mind the occasional triple cocktail night.
Neighborhood: Ukrainian Village MAP

Weegee's Lounge
If you hate spending $14 for a cocktail, Logan Square's low-lit, hardly ever super-crowded bar—named after the infamous 1930's and 40's NYC crime scene photographer—will be your new go-to destination. Bartenders at this unsung cocktail spot churn out signature whiskey cocktails, like the Lion's Tail, which combines bourbon, pimento dram, lime juice, simple syrup, and Angostrua bitters—which pairs perfectly with a few rounds or two of shuffleboard at this low-key neighborhood mainstay.
Neighborhood: Logan Square MAP

Little Bad Wolf
Even if you're coming for the game-changing triple-patty burger, Japanese BBQ pork bao, or steak frites, you'll discover there's a definite bar vibe at this Andersonville spot. Aside from the filling fare, the copper bar at the restaurant's core slings expertly crafted specialty cocktails with house-made ingredients and fresh juices that'll keep you here until the wee hours of the morning. Try the gorgeous Morso di Morte, a mix of apple brandy, ginger-infused Cocchi Americano, lemon, malbec, and Aphrodite bitters, topped with a dehydrated apple. Otherwise, their new LBW Boulevardier will surely make you jump for joy.
Neighborhood: Andersonville MAP

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