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  1. 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.

  2. Photograph: Chloe List
    Photograph: Chloe List

    Bella Mela at Nico Osteria
    Bella Mela, from Nico bartender Matty Eggleston, means “beautiful apple” in Italian, and it’s a very autumnal combination of apple brandy, vermouth, orange peel liqueur, apple cider and chocolate bitters.

  3. Photograph courtesy Sable
    Photograph courtesy Sable

    Gravity Storm at Sable Kitchen & Bar
    Sable bartender Chris Cavarra’s cocktail is made with apple brandy, vermouth, cinnamon-cranberry syrup, lemon and Fee’s Old Fashioned Bitters, and shaken and poured over ice.

  4. Photograph courtesy Acadia
    Photograph courtesy Acadia

    Smashin’ at Acadia
    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.

  5. Photograph: Chloe List
    Photograph: Chloe List

    Mary in the Library at the Violet Hour
    Bartender Patrick Smith’s rich, creamy cocktail uses Unicum Plum, a Hungarian bitter liqueur that’s aged with plums, along with gin, chocolate liqueur, egg and nutmeg.

  6. Photograph: Martha Williams
    Photograph: Martha Williams

    Pie-Eyed in Polynesia at Fat Rice
    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.

  7. Photograph: Martha Williams
    Photograph: Martha Williams

    A Couple Few Figs at Fountainhead
    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.

  8. Photograph: Katie Basil
    Photograph: Katie Basil

    Fear and Desire at Drumbar
    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.

  9. Photograph courtesy La Sirena Clandestina
    Photograph courtesy La Sirena Clandestina

    The Ancho-Cola at La Sirena Clandestina
    For a spicy fall drink, beverage director Derek Payne mixes ancho chili liqueur, Italian vermouth and lemon, then adds bitterness from orange bitters and Chinotto soda.

  10. Photograph: Rachel Oftedahl
    Photograph: Rachel Oftedahl

    Savant Sour at CH Distillery
    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.

  11. Photograph: Matthias Merges
    Photograph: Matthias Merges

    Highing Fly at A10
    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.

  12. Photograph: Jessica Lynn Capron
    Photograph: Jessica Lynn Capron

    Core Power at the Dawson
    Get your veggies in with the Core Power, which spikes kale-apple juice with apple brandy, genever and yellow chartreuse, then balances it with honey, lime and celery bitters.

  13. Photograph: Matthias Merges
    Photograph: Matthias Merges

    Ichabod Cranium at Billy Sunday
    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.

  14. Photograph: Chloe List
    Photograph: Chloe List

    Rum Rebellion at Blackbird
    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.

  15. Photograph courtesy Barrelhouse Flat
    Photograph courtesy Barrelhouse Flat

    Kiss Gamble at Barrelhouse Flat
    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.

  16. Photograph: Lindsey Becker
    Photograph: Lindsey Becker

    Woolworth's Manhattan at Henry’s Swing Club
    Beverage director Michael Rubel doctors the traditional Manhattan by adding bittersweet Cynar and root beer bitters to Wild Turkey 101 and vermouth.

  17. Hookshot Sour at Mott St.
    Mott St.’s fall cocktail menu includes this drink that mixes bourbon and Amargo Vallet Angostura Amaro (a Mexican liqueur) with apple, sesame leaf and lemon.

  18. Photograph courtesy Punch House
    Photograph courtesy Punch House

    Charles Dickens Punch at Punch House
    Warm up in Punch House’s cozy basement with this hot punch, made with rum, brandy, tea, sugar and lemon. It’s based on a recipe by Charles Dickens himself.

  19. Panama at Tortoise Club
    Made with Chopin Rye Vodka, lemon, Lillet, coconut liqueur, mint and a double hit of bitters—both Angostura and baked apple bitters—this is one hefty cocktail.

  20. Photograph courtesy Sepia
    Photograph courtesy Sepia

    Jack Rosie at Sepia
    Bartender Griffin Elliot gives the classic Jack Rose a fall spin by using spiced grenadine and apple brandy, rather than the usual applejack and grenadine.

  21. The Window Swill at Longman & Eagle 
    The cocktail, which can be served hot or cold, features bourbon, apple cider reduction and caramel. It also includes Flaming Sphere, the housemade version of Fireball, which is made with cinnamon, Madagascar vanilla bean, green cardamom, star anise, clove, allspice berry, black pepper and juniper. The drink, inspired by Bang Bang Pie’s apple pie with caramelized cheddar crust, also has a caramelized cheddar rim.

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

Acadia
  • Restaurants
  • Contemporary American
  • Near South Side
  • price 4 of 4

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.

  • Restaurants
  • Italian
  • Hyde Park
  • price 3 of 4

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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The Barrelhouse Flat
  • Bars
  • Cocktail bars
  • Sheffield & DePaul
  • price 2 of 4

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.

  • Bars
  • Cocktail bars
  • Logan Square
  • price 2 of 4

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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  • Restaurants
  • 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.

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  • Bars
  • 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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  • Restaurants
  • 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.

  • Bars
  • 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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