clock menu more-arrow no yes
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

View as Map
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.

Read More
Note: Restaurants on this map are listed geographically.

1. Rogers Park Social

Copy Link
6920 N Glenwood Ave
Chicago, IL 60626
(773) 791-1419
Visit Website

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.

2. Larry's

Copy Link
In Lobby, 1020 W Lawrence Ave
Chicago, IL 60640
(872) 873-1001
Visit Website

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.

3. The Sixth

Copy Link
2202 W Lawrence Ave
Chicago, IL 60625
(312) 256-2960
Visit Website

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.

4. Elixir Lounge

Copy Link
3452 N Halsted St
Chicago, IL 60657
(773) 975-9244
Visit Website

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.

5. Nisei Lounge

Copy Link
3439 N Sheffield Ave
Chicago, IL 60657
(773) 525-0557
Visit Website

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.”

6. Billy Sunday

Copy Link
3143 W Logan Blvd
Chicago, IL 60647
(773) 661-2485
Visit Website

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.

7. The Whistler

Copy Link
2421 N Milwaukee Ave
Chicago, IL 60647
(773) 227-3530
Visit Website

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.

8. Scofflaw

Copy Link
3201 W Armitage Ave
Chicago, IL 60647
(773) 252-9700
Visit Website

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.

9. The Violet Hour

Copy Link
1520 N Damen Ave
Chicago, IL 60622
(773) 252-1500
Visit Website

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.

10. Fame Supper Club

Copy Link
157 W Ontario St
Chicago, IL 60654
(312) 766-7050
Visit Website

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

11. Bar Sótano

Copy Link
In the alley behind Frontera Grill, 443 N Clark St
Chicago, IL 60654
(312) 391-5857
Visit Website

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.

12. Blank's Bar

Copy Link
355 N Clark St
Chicago, IL 60654

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.

13. Bar Pendry Chicago

Copy Link
81 E Wacker Pl
Chicago, IL 60601
(312) 777-9000
Visit Website

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

14. Kumiko

Copy Link
630 W Lake St
Chicago, IL 60661
(312) 285-2912
Visit Website

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

15. Moneygun

Copy Link
660 W Lake St
Chicago, IL 60661
(312) 600-0600
Visit Website

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.

16. Little Goat Diner

Copy Link
820 W Randolph St
Chicago, IL 60607
(312) 888-3455
Visit Website

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.

17. Bandit

Copy Link
841 W Randolph St
Chicago, IL 60607
(312) 666-6061
Visit Website

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.

18. Osito's Tap

Copy Link
2553 S Ridgeway Ave
Chicago, IL 60623
(773) 277-8117
Visit Website

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

19. The Duck Inn

Copy Link
2701 S Eleanor St
Chicago, IL 60608
(312) 724-8811
Visit Website

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

20. Mesler Kitchen | Bar | Lounge

Copy Link
1401 E 53rd St
Chicago, IL 60615
(773) 289-1005
Visit Website

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.

1. Rogers Park Social

6920 N Glenwood Ave, Chicago, IL 60626

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.

6920 N Glenwood Ave
Chicago, IL 60626

2. Larry's

In Lobby, 1020 W Lawrence Ave, Chicago, IL 60640

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.

In Lobby, 1020 W Lawrence Ave
Chicago, IL 60640

3. The Sixth

2202 W Lawrence Ave, Chicago, IL 60625

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.

2202 W Lawrence Ave
Chicago, IL 60625

4. Elixir Lounge

3452 N Halsted St, Chicago, IL 60657

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.

3452 N Halsted St
Chicago, IL 60657

5. Nisei Lounge

3439 N Sheffield Ave, Chicago, IL 60657

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.”

3439 N Sheffield Ave
Chicago, IL 60657

6. Billy Sunday

3143 W Logan Blvd, Chicago, IL 60647

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.

3143 W Logan Blvd
Chicago, IL 60647

7. The Whistler

2421 N Milwaukee Ave, Chicago, IL 60647

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.

2421 N Milwaukee Ave
Chicago, IL 60647

8. Scofflaw

3201 W Armitage Ave, Chicago, IL 60647

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.

3201 W Armitage Ave
Chicago, IL 60647

9. The Violet Hour

1520 N Damen Ave, Chicago, IL 60622

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.

1520 N Damen Ave
Chicago, IL 60622

10. Fame Supper Club

157 W Ontario St, Chicago, IL 60654
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.

157 W Ontario St
Chicago, IL 60654

11. Bar Sótano

In the alley behind Frontera Grill, 443 N Clark St, Chicago, IL 60654

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.

In the alley behind Frontera Grill, 443 N Clark St
Chicago, IL 60654

12. Blank's Bar

355 N Clark St, Chicago, IL 60654

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.

355 N Clark St
Chicago, IL 60654

13. Bar Pendry Chicago

81 E Wacker Pl, Chicago, IL 60601
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.

81 E Wacker Pl
Chicago, IL 60601

14. Kumiko

630 W Lake St, Chicago, IL 60661
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.”

630 W Lake St
Chicago, IL 60661

15. Moneygun

660 W Lake St, Chicago, IL 60661

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.

660 W Lake St
Chicago, IL 60661

Related Maps

16. Little Goat Diner

820 W Randolph St, Chicago, IL 60607

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.

820 W Randolph St
Chicago, IL 60607

17. Bandit

841 W Randolph St, Chicago, IL 60607

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.

841 W Randolph St
Chicago, IL 60607

18. Osito's Tap

2553 S Ridgeway Ave, Chicago, IL 60623
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.

2553 S Ridgeway Ave
Chicago, IL 60623

19. The Duck Inn

2701 S Eleanor St, Chicago, IL 60608
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.

2701 S Eleanor St
Chicago, IL 60608

20. Mesler Kitchen | Bar | Lounge

1401 E 53rd St, Chicago, IL 60615

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.

1401 E 53rd St
Chicago, IL 60615

Related Maps