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
Old Fashioned at Longman & Eagle
Phortograph: Clayton Hauck
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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

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Old Fashioned at Longman & Eagle
Phortograph: Clayton Hauck
Restaurants, Contemporary American

Old Fashioned at Longman & Eagle's OSB

icon-location-pin Logan Square

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


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Old Fashioned at Billy Sunday
Photograph: Matthias Merges
Bars, Cocktail bars

Old Fashioned at Billy Sunday

icon-location-pin Logan Square

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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3
Old Fashioned at Violet Hour
Photograph: Sandy Noto
Bars, Cocktail bars

Old Fashioned at the Violet Hour

icon-location-pin Wicker Park

For an old-fashioned that you can feel good about drinking, the Violet Hour comes through. It's simple but solid, with House Elijah Craig Bourbon, demerara and Angostura bitters. —EA

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Photograph: Neil Burger
Bars, Cocktail bars

Old Fashioned at 1952 1/2 Liquorette

icon-location-pin 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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5
Photograph: Eugene (Huge) Galdones
Bars, Cocktail bars

Nothing Noble at the Loyalist

icon-location-pin West Loop
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
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Old Fashioned at Cindy's
Photograph: Kelsey Sullivan
Restaurants, Contemporary American

Old Fashioned at Cindy's

icon-location-pin Loop

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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Old Fashioned at Pearl's Southern Comfort
Photograph: Courtesy Pearl's
Restaurants, Soul and southern American

Barrel Aged Gin Old Fashioned at Pearl's Southern Comfort

icon-location-pin Edgewater

A different take on an old-fashioned, Pearl's Southern Comfort uses Ballast Point's Barrel Rested Old Grove gin, aged in oak barrels to give it an oaky and woody taste. The gin makes it a lighter-bodied drink, a smooth sipper with sugar, orange and garnished with a few cherries. —EA

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Old Fashioned at Longman & Eagle
Photograph: Clayton Hauck
Bars, Lounges

Old Fashioned at the Game Room

icon-location-pin Loop

After hanging out at Cindy's head downstairs for a no-frills version of an old-fashioned. It's a great blend of bourbon with demerara sugar and bitters. With a twist of orange on top, this spirited cocktail is gonna help you be on your best shuffleboard game. —EA

Make it at home

The Summit Bar old fashioned
Photograph: Noah Fecks
Bars

How to make an old-fashioned

One of the most simple, elemental creations in the tome of classic cocktails, the old-fashioned is the whiskey lover's gateway to the world of drinking

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