Photograph: Martha Williams
Photograph: Martha Williams |

Grape Gimlet at Vera
The Spanish restaurant’s fall cocktail list includes the Grape Gimlet, which sommelier/owner Liz Mendez makes with Concord grapes from Michigan’s Mick Klug Farm. Mendez adds the grape syrup to Small’s Gin and lime juice for a sweet and tart cocktail.

21 new fall cocktails to try

This season, Chicago bartenders are mixing up fall cocktails with cider, apple brandy, figs and grapes. One spot is even serving a cocktail inside a giant pumpkin

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After a summer of slushies and frozen drinks, it's time to ease into fall with cocktails heavy on fall flavors. Chicago bartenders are embracing the season with apples, Concord grapes and cranberries, plus more surprising things like housemade Fireball and pumpkin serving vessels. Here are 21 new fall cocktails to try.

RECOMMENDED: Our guide to fall in Chicago

New fall cocktails in Chicago

  • Contemporary American
  • Near South Side
  • price 4 of 4
  • Recommended
Acadia
Acadia
Smashin’ 
Crab apples are the star of bartender Arunas Bruzas’s cocktail—he muddles the fruit to make a crab apple and mint soda, then adds gin and aperol.
  • Italian
  • Hyde Park
  • price 3 of 4
  • Recommended
Highing Fly
A10 barkeep Alex Bachman will be releasing the fall cocktail menu on October 29, and drinks include the Highing Fly, made with tequila, chili, cider reduction and citrus.
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  • Cocktail bars
  • Sheffield & DePaul
  • price 2 of 4
The Barrelhouse Flat
The Barrelhouse Flat
Kiss Gamble
Jessica Tessendorf’s boozy new cocktail mixes JK Scrumpy's Winterruption hard cider with rum, amaro and arrack, then balances it with lime and falernum.
  • Cocktail bars
  • Logan Square
  • price 2 of 4
  • Recommended
Ichabod Cranium
It doesn’t get much more autumnal than drinking out of a pumpkin. At Billy Sunday, the Ichabod Cranium stuffs bourbon ice, applejack/cider fizz and vermouth into a pumpkin and sets it on fire. It’s $80, but serves three to eight people.
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  • Contemporary American
  • West Loop
  • price 4 of 4
Rum Rebellion
Love rum? Here you go: Kyle Davidson is mixing Plantation 3 Stars Rum and El Dorado 5-year with pineapple juice and allspice dram. It’s a riff on the Hotel Nacional, a Cuban cocktail.
  • Cocktail bars
  • West Loop
  • price 2 of 4
  • Recommended
Savant Sour
CH Distillery just launched its new aquavit (an herbal, Scandinavian liqueur) this week, and it's showcasing it in a cocktail with sage, simple syrup and egg white.
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  • Cocktail bars
  • Streeterville
  • price 3 of 4
Fear and Desire
Inspired by corn pudding, Drumbar’s new fall cocktail starts with roasted corn-infused mezcal. Added to that are a couple of amari, vanilla, salt, an egg and Angostura bitters, which add bitterness and roundess. It’s finished off with a sprinkle of grated cinnamon.
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  • South Asian
  • Logan Square
  • price 2 of 4

Pie-Eyed in Polynesia
Fat Rice’s tiki-inspired fall cocktail begins with a base of equal parts rum and apple cider, then adds sherry, maraschino liqueur, lemon and both Angostura and Bittercube Cherry Bark & Vanilla Bitters. It’s garnished with a pickled crab apple.

  • Beer bars
  • Lincoln Square
  • price 2 of 4
A Couple Few Figs
Fountainhead has a great whiskey selection, and this fall it's infusing FEW Bourbon with figs, then adding ruby port, maple syrup and angostura bitters to round out the cocktail. It’s garnished with a maple syrup and bourbon–soaked sour cherry.
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