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Old Fashioned at Longman & Eagle
Phortograph: Clayton Hauck

The 8 best old-fashioneds in Chicago

Find the best spots in Chicago for one of the most popular and delicious classic cocktails, the old-fashioned

Written by
Elizabeth Atkinson
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Sometimes, you don't want to think too hard about your cocktail. You just want to pull up a seat at the bar, order some bar snacks and have a solid, well-balanced and well-mixed drink. Cue the old-fashioned—a great classic cocktail that highlights the bite of whiskey (like its other classic cocktail friend, the Manhattan) with a perfect hint of sweetness and citrus. You can find them most places, but we dug up some of the best in the city.

RECOMMENDED: Our guide to cocktails in Chicago

  • Restaurants
  • Contemporary American
  • Logan Square
  • price 2 of 4

Longman & Eagle is well-known for its stellar food menu, but the bar out back (OSB) serves up a great, simple lineup of cocktails. The old-fashioned is no exception. Made with Buffalo Trace bourbon, three types of bitters, demerara and topped off with a touch of orange and lemon oil, it’s a delightful way to consume whiskey. —Clayton Guse


  • Bars
  • Cocktail bars
  • Logan Square
  • price 2 of 4
This full-bodied twist on a classic is an old-fashioned in name and flavor, but its recipe only looks vaguely like the cocktail it's named for. It's filled with bourbon and cube sugar, but Billy Sunday adds Rabarbaro, a rhubarb liqueur, and other essential oils to add a little more body to the drink. —Elizabeth Atkinson
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  • Bars
  • Cocktail bars
  • Bucktown
You'll find this southern-style whiskey bar in the back of Dixie, with a lush leather banquette and marble tables. Cocktails come with a twist on southern favorites, like the suissesse and a julep. We like the Old Fashioned, with 1952 1/2 Elijah Craig Selection, sugar and sarsparilla bitters. It's just a bit different with the comfort we search for in an Old Fashioned. —EA
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  • Bars
  • Cocktail bars
  • West Loop
  • price 3 of 4
The Nothing Noble has elements of an old-fashioned, with a bit of a twist. It's packed with bourbon, sweetened with demerara sugar, bittered with Amargo Vallet bitters, lemons and verbena for a refreshing kick. We think it's just right for cozying up in this dark lounge for the night, whether you kick your night off with it or hang out for the evening while munching on some seasonal snacks. —EA
  • Restaurants
  • Contemporary American
  • Loop
  • price 3 of 4
With pretty views, hanging out on the rooftop at Cindy's is easy and the old-fashioned makes it even easier. Made with Old Forester 1897, demerara, Angostura bitters and garnished with an orange peel, this old-fashioned will please even a hardcore Manhattan drinker. —EA
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