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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

 (Photograph: Martha Williams)
1/21
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.

 (Photograph: Chloe List)
2/21
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.

 (Photograph courtesy Sable)
3/21
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.

 (Photograph courtesy Acadia)
4/21
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.

 (Photograph: Chloe List)
5/21
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.

 (Photograph: Martha Williams)
6/21
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.

 (Photograph: Martha Williams)
7/21
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.

 (Photograph: Katie Basil)
8/21
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.

 (Photograph courtesy La Sirena Clandestina)
9/21
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.

 (Photograph: Rachel Oftedahl)
10/21
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.

 (Photograph: Matthias Merges)
11/21
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.

 (Photograph: Jessica Lynn Capron)
12/21
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.

 (Photograph: Matthias Merges)
13/21
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.

 (Photograph: Chloe List)
14/21
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.

 (Photograph courtesy Barrelhouse Flat)
15/21
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.

 (Photograph: Lindsey Becker)
16/21
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.

17/21

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.

 (Photograph courtesy Punch House)
18/21
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.

19/21

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.

 (Photograph courtesy Sepia)
20/21
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.

21/21

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.

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

Recommended

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.

Book now Read more
Near South Side

A10

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.

Book now Read more
Hyde Park

The Barrelhouse Flat

Recommended

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.

Read more
Sheffield & DePaul
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Billy Sunday

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.

Read more
Logan Square

Blackbird

Recommended

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.

Book now Read more
West Loop

CH Distillery

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.

Read more
West Loop
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The Dawson

Core Power
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.

Book now Read more
River West/West Town

Drumbar

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.

Read more
Streeterville

Fat Rice

Recommended

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.

Read more
Logan Square
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Fountainhead

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.

Read more
Lincoln Square
Show more

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