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A cocktail in a short glass with a sugared rim and lime garnish on a table with a backdrop of colorful leaves and a round white gourd.
Blank’s Bar, aka Autumn’s Bar in October.
DineAmic Hospitality

Chicago’s Best Fall Cocktails

When the weather turns chilly, it’s time to embrace dark liquor and warming spices — and pumpkin

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Blank’s Bar, aka Autumn’s Bar in October.
| DineAmic Hospitality

When there’s a nip in the air, leaves crunching underfoot, and the thought of sweaters and flannel no longer feels oppressive, one’s tastebuds develop a yearning for the darker liquors and the warmer spices. Mixologists all over town have obliged with cocktails that incorporate bourbon and whiskey with notes of cinnamon, cloves, nutmeg, and allspice, not to mention apple cider and pumpkin puree. And some add smoke and magic, because what else can you expect around Halloween? Here’s a list of some of the city’s most autumnal spirits.

As of August 20, the city has mandated that everyone wear facial coverings while indoors. For updated information on coronavirus cases, please visit the city of Chicago’s COVID-19 dashboard. Health experts consider dining out to be a high-risk activity for the unvaccinated; the latest data about the delta variant indicates that it may pose a low-to-moderate risk for the vaccinated, especially in areas with substantial transmission. The latest CDC guidance is here; find a COVID-19 vaccination site here.

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Rogers Park Social

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RP Social changes up its cocktail menu every season and has been mixing up the fall drinks all month. Try the Mexcapple — baked apple-infused El Buel Mezcal, Hardin’s Family Farm apple cider, lemon, soda — or, on a chilly evening, the Fig NewToddy, made with bourbon, fig grape liqueur, and hot water and served with a Fig Newton. Cocktails are also available to go.

Larry's

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Larry’s has a bottler for its cocktails now, and will be offering special Thanksgiving and Christmas-themed drinks to go, for those who prefer to enjoy the holiday spirit in the comfort of their own homes.

The Sixth

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This Ravenswood bar from the Fifty/50 group really gets into the Halloween spirit, with a full menu of witchy cocktails, including the Sanderson Sour, made with Reposado mezcal, pomegranate, raspberry, violet, lime, and, most intriguingly, magic.

Elixir Lounge

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The fall menu at this Lakeview cocktail bar was inspired by the unpredictable weather of the fall equinox, from Maple Ginger Thyme (El Dorado 12-year aged rum, ginger infused maple syrup, lime, thyme), which conjures a sunny afternoon amid the changing leaves, to the Nor’Easter (Deep Eddy Vodka, St. George spiced pear, lime, ginger beer, and Blackstrap rum), a dark and stormy night.

Nisei Lounge

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Someone had to create a pumpkin spice Malört shot, and that someone is the staff at the Nisei Lounge, the Wrigleyville dive bar, who promise: “It can’t be any worse than Nisei Labs 2019 Halloween Peeps infused Malort. Probably.”

Billy Sunday

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Billy Sunday has updated its menu to include autumnal cocktails, including the Camino — a blend of apple and pear brandy, cinnamon, lemon, amaro, allspice, pear bitters, and calamansi vinegar — and Fisticuffs — barrel aged rye gin, switchel, cava, apertif wine, Tepache honey, spiced pear and absinthe. Select cocktails are also available to go.

The Whistler

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The Whistler just reopened at the end of September with a new beverage director, Alex Barbatsis, and a cocktail menu that changes daily, incorporating seasonal flavors and spirits; follow along on Instagram.

Scofflaw

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Originally a gin bar, Scofflaw has expanded its menu to include other spirits and some legitimately good food. The fall cocktail list does incorporate lots of gin, but also corn whiskey, and vermouth. The Steel Cut evokes the flavors of oatmeal, with genever, sherry, oat orgeat, lemon, allspice dram, and old fashioned bitters.

The Violet Hour

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In addition to offering seasonal cocktails at its speakeasy-style bar, The Violet Hour is also selling a series of fall-themed subscription boxes for delivery. Halloween is a collection of “spooky” cocktails throughout history (White Witch, Corpse Reviver), while Thanksgiving focuses on the drinks of colonial America (Sangaree, Crambambull), and Christmas recreates Victorian London with Dickensian punches.

Fame Supper Club

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The Roaring ’20s-themed nightclub pays tribute to the famous 1920 Lady in the Ashes murder case with a cocktail of the same name, made with Ron Matusalem dark rum, muddled cantaloupe, coconut cream, simple syrup, fresh lime juice, and activated charcoal.

A gray drink in a tall glass topped by a spray of white flowers
Lady in the Ashes.
Fame Supper Club

Bar Sótano

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This fall, Lainie Bayless’s cocktail menu at Bar Sótano features lots of apple, including a Hot Butter Whisky Cider, made with Abasolo whisky (infused with brown butter), Montelobos espadín mezcal, BroVo boomerang, piloncillo, Amargo Vallet, and local apple cider.

Blank's Bar

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Blank’s Bar has disguised itself for the season as Autumn’s Bar, a month-long pop-up that began October 1. The menu features an alcoholic take on the PSL called The Basic B*#ch that contains Tito’s, Kahlúa, pumpkin spice, and vanilla oat milk.

Bar Pendry Chicago

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This cocktail bar in the Pendry Hotel in the Carbon & Carbide Building also spruced up its menu for fall, including the Printers Row, containing Ron Zacapa 23-year rum, Amaro Sfumato, and espresso.

A lounge with an armchair at a right angle to a long leather sofa, with a round coffee table and a fireplace in the background.
Bar Pendry.
Barry Brecheisen

Typical of Kumiko, owner-mixologist Julia Momosé combines fall in Japan and the Midwest in Highball No. 3, billed as “whisky from Japan with apples of the Midwest and a tinge of smoke.”

A small bar with stools in front and bottles on shelves behind
Kumiko.
Kumiko

Moneygun

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Moneygun in the West Loop has moved beyond pumpkin. The seasonal drink Just Like Mom Used to Make incorporates acorn squash instead, along with El Dorado three-year rum, Pierre Ferrand Cognac, and brown sugar.

Little Goat Diner

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Most of Little Goat’s Halloween festivities are geared toward children, but sometimes adults need to celebrate, too, in the form of the Sleepy Hollow cocktail: pumpkin-spiced infused Evan Williams, cold brew, and Coco Lopez cold foam.

This West Loop bar is celebrating Halloween with a bottomless brunch, but it’s also offering special cocktails all month long, including Fall’s Alibi, a mixture of Patron Silver, Pama liqueur, apple cider, and pomegranate.

Osito's Tap

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Osito’s celebrates fall with the Automnal cocktail: Paranubes Oaxaca rum, mazanilla sherry, ginger honey, lime, and apple bitters. Raise one in memory of the original Osito, the chihuahua for whom the bar is named, who died earlier this year.

A man holding a menu seated in a booth with a chihuahua.
Owner Mike Moreno Jr. and Osito.
Barry Brecheisen

The Duck Inn

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Fall cocktails can be non-alcoholic. One of the house kombuchas at Bridgeport’s Duck Inn this month is Canadian Maple Noir Apple Cider. But maple cider also plays a role in one of the alcoholic drinks, Big Salty Tears.

A long wooden bar with yellow stools in the foreground, lamps overhead, and shelves full of liquor bottles on the back wall.
The Duck Inn.
Barry Brecheisen

Mesler Kitchen | Bar | Lounge

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Instead of creating a whole new seasonal menu, Mesler dresses up its regular drinks in fall colors: a pear margarita, an apple sidecar, and a pumpkin sidecar. There’s also a hot toddy to ward off chilly weather.

Rogers Park Social

RP Social changes up its cocktail menu every season and has been mixing up the fall drinks all month. Try the Mexcapple — baked apple-infused El Buel Mezcal, Hardin’s Family Farm apple cider, lemon, soda — or, on a chilly evening, the Fig NewToddy, made with bourbon, fig grape liqueur, and hot water and served with a Fig Newton. Cocktails are also available to go.

Larry's

Larry’s has a bottler for its cocktails now, and will be offering special Thanksgiving and Christmas-themed drinks to go, for those who prefer to enjoy the holiday spirit in the comfort of their own homes.

The Sixth

This Ravenswood bar from the Fifty/50 group really gets into the Halloween spirit, with a full menu of witchy cocktails, including the Sanderson Sour, made with Reposado mezcal, pomegranate, raspberry, violet, lime, and, most intriguingly, magic.

Elixir Lounge

The fall menu at this Lakeview cocktail bar was inspired by the unpredictable weather of the fall equinox, from Maple Ginger Thyme (El Dorado 12-year aged rum, ginger infused maple syrup, lime, thyme), which conjures a sunny afternoon amid the changing leaves, to the Nor’Easter (Deep Eddy Vodka, St. George spiced pear, lime, ginger beer, and Blackstrap rum), a dark and stormy night.

Nisei Lounge

Someone had to create a pumpkin spice Malört shot, and that someone is the staff at the Nisei Lounge, the Wrigleyville dive bar, who promise: “It can’t be any worse than Nisei Labs 2019 Halloween Peeps infused Malort. Probably.”

Billy Sunday

Billy Sunday has updated its menu to include autumnal cocktails, including the Camino — a blend of apple and pear brandy, cinnamon, lemon, amaro, allspice, pear bitters, and calamansi vinegar — and Fisticuffs — barrel aged rye gin, switchel, cava, apertif wine, Tepache honey, spiced pear and absinthe. Select cocktails are also available to go.

The Whistler

The Whistler just reopened at the end of September with a new beverage director, Alex Barbatsis, and a cocktail menu that changes daily, incorporating seasonal flavors and spirits; follow along on Instagram.

Scofflaw

Originally a gin bar, Scofflaw has expanded its menu to include other spirits and some legitimately good food. The fall cocktail list does incorporate lots of gin, but also corn whiskey, and vermouth. The Steel Cut evokes the flavors of oatmeal, with genever, sherry, oat orgeat, lemon, allspice dram, and old fashioned bitters.

The Violet Hour

In addition to offering seasonal cocktails at its speakeasy-style bar, The Violet Hour is also selling a series of fall-themed subscription boxes for delivery. Halloween is a collection of “spooky” cocktails throughout history (White Witch, Corpse Reviver), while Thanksgiving focuses on the drinks of colonial America (Sangaree, Crambambull), and Christmas recreates Victorian London with Dickensian punches.

Fame Supper Club

A gray drink in a tall glass topped by a spray of white flowers
Lady in the Ashes.
Fame Supper Club

The Roaring ’20s-themed nightclub pays tribute to the famous 1920 Lady in the Ashes murder case with a cocktail of the same name, made with Ron Matusalem dark rum, muddled cantaloupe, coconut cream, simple syrup, fresh lime juice, and activated charcoal.

A gray drink in a tall glass topped by a spray of white flowers
Lady in the Ashes.
Fame Supper Club

Bar Sótano

This fall, Lainie Bayless’s cocktail menu at Bar Sótano features lots of apple, including a Hot Butter Whisky Cider, made with Abasolo whisky (infused with brown butter), Montelobos espadín mezcal, BroVo boomerang, piloncillo, Amargo Vallet, and local apple cider.

Blank's Bar

Blank’s Bar has disguised itself for the season as Autumn’s Bar, a month-long pop-up that began October 1. The menu features an alcoholic take on the PSL called The Basic B*#ch that contains Tito’s, Kahlúa, pumpkin spice, and vanilla oat milk.

Bar Pendry Chicago

A lounge with an armchair at a right angle to a long leather sofa, with a round coffee table and a fireplace in the background.
Bar Pendry.
Barry Brecheisen

This cocktail bar in the Pendry Hotel in the Carbon & Carbide Building also spruced up its menu for fall, including the Printers Row, containing Ron Zacapa 23-year rum, Amaro Sfumato, and espresso.

A lounge with an armchair at a right angle to a long leather sofa, with a round coffee table and a fireplace in the background.
Bar Pendry.
Barry Brecheisen

Kumiko

A small bar with stools in front and bottles on shelves behind
Kumiko.
Kumiko

Typical of Kumiko, owner-mixologist Julia Momosé combines fall in Japan and the Midwest in Highball No. 3, billed as “whisky from Japan with apples of the Midwest and a tinge of smoke.”

A small bar with stools in front and bottles on shelves behind
Kumiko.
Kumiko

Moneygun

Moneygun in the West Loop has moved beyond pumpkin. The seasonal drink Just Like Mom Used to Make incorporates acorn squash instead, along with El Dorado three-year rum, Pierre Ferrand Cognac, and brown sugar.

Related Maps

Little Goat Diner

Most of Little Goat’s Halloween festivities are geared toward children, but sometimes adults need to celebrate, too, in the form of the Sleepy Hollow cocktail: pumpkin-spiced infused Evan Williams, cold brew, and Coco Lopez cold foam.

Bandit

This West Loop bar is celebrating Halloween with a bottomless brunch, but it’s also offering special cocktails all month long, including Fall’s Alibi, a mixture of Patron Silver, Pama liqueur, apple cider, and pomegranate.

Osito's Tap

A man holding a menu seated in a booth with a chihuahua.
Owner Mike Moreno Jr. and Osito.
Barry Brecheisen

Osito’s celebrates fall with the Automnal cocktail: Paranubes Oaxaca rum, mazanilla sherry, ginger honey, lime, and apple bitters. Raise one in memory of the original Osito, the chihuahua for whom the bar is named, who died earlier this year.

A man holding a menu seated in a booth with a chihuahua.
Owner Mike Moreno Jr. and Osito.
Barry Brecheisen

The Duck Inn

A long wooden bar with yellow stools in the foreground, lamps overhead, and shelves full of liquor bottles on the back wall.
The Duck Inn.
Barry Brecheisen

Fall cocktails can be non-alcoholic. One of the house kombuchas at Bridgeport’s Duck Inn this month is Canadian Maple Noir Apple Cider. But maple cider also plays a role in one of the alcoholic drinks, Big Salty Tears.

A long wooden bar with yellow stools in the foreground, lamps overhead, and shelves full of liquor bottles on the back wall.
The Duck Inn.
Barry Brecheisen

Mesler Kitchen | Bar | Lounge

Instead of creating a whole new seasonal menu, Mesler dresses up its regular drinks in fall colors: a pear margarita, an apple sidecar, and a pumpkin sidecar. There’s also a hot toddy to ward off chilly weather.

Related Maps