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Scofflaw’s fall cocktail selection.
Jude Goergen

Where to Drink Tempting Fall Cocktails in Chicago Right Now

Hit these 13 bars for seasonal elixirs with pumpkin, apple, and more fall flavors

by Kat Odell
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Scofflaw’s fall cocktail selection.
| Jude Goergen
by Kat Odell
1 comment / new

As bright and juicy summer ingredients fade out of season, warm fall flavors set into Chicago bars. That means pumpkin, cinnamon, apple, and more are often mixed and muddled into a seemingly endless roster of new fall cocktails. Autumn also signals the onset of Starbucks’ cultist Pumpkin Spice Latte, and at least one bar mentioned below is serving an elevated, booze-spiked take.

Rich in dark spirits like whiskey, brandy, and rum, the below mentioned bars are among the best places to sip the flavors of fall in cocktail form.

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Tinker To Evers

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The first cocktail menu from newbie basement bar Tinker To Evers, which debuted below Detroit-style pizzeria Union Full Board earlier this month in Wrigleyville, entirely channels fall. Here one will find a bevy of fall-forward flavors, like sherry, thyme liquor, walnut, and celery bitters. Try tipples like Leche Di Tigre (Nola Chicory Liquor, horchata, and walnut bitters), and Mr. Sunshine (Bols Genever gin, thyme liqueur, lemon, and Angostura bitters).

3473 N Clark St, Chicago, IL 60657
(773) 248-9001
(773) 248-9001
Inside Tinker To Evers
Tinker To Evers [Official Photo]

Longman & Eagle

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Logan Square fixture Longman & Eagle’s seasonal fall drinks list is out. Devised by the gastropub’s bar team, lead by beverage director Tony Correale and bar managers Nathan Case-McDonald and Jake Dean, come in for drinks like Clock Without Hands (Very Old Barton Bonded, Amer Gingembre, genmaicha green tea, yuzu honey, lemon) and The Kentucky Kick-start (Maker’s Mark Private Select Red Top, Dark Matter coffee, Cap Corse Blanc, honey, lemon).

2657 N Kedzie Ave, Chicago, IL 60647
(773) 276-7110
(773) 276-7110
Longman & Eagle
Clayton Hauck

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Billy Sunday

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Beloved Logan Square drinking den Billy Sunday launched its fall libation list with standouts by bar manager Stephanie Andrews including a play on Starbucks’ PSL reworked into an autumnal milk punch served in a pumpkin (rum, bourbon, pumpkin pie spice, rooibos tea, and lemon) for four to six imbibers, and Papa Don’t Peach (whiskey, smoked peaches, fig wood, lemon, and egg white), served in a Russian doll.

3143 W Logan Blvd, Chicago, IL 60647
(773) 661-2485
(773) 661-2485
Billy Sunday’s Papa Don’t Peach cocktail.
Billy Sunday [Official Photo]

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Quiote/Todos Santos

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Chicago’s most expansive collection of small-production mezcal lives at Todos Santos, the subterranean bar below Logan Square’s Mexican eatery, Quiote. And while smoky mezcal itself makes for a warming seasonal sipper, in September barman Jay Schroeder’s new drinks list rolled out, with creations like Life During Wartime (apricot cordial, Scotch, mezcal, house-made pasilla chili-rooibos syrup, and bitter orange juice) and Check My SoundCloud (sotol, chili liqueur, absinthe, lemon, canola, and hoja santa salt).

2456 N California Ave, Chicago, IL 60647
(312) 878-8571
(312) 878-8571
Todos Santos’ Life During Wartime
Quiote/Todos Santos [Official Photo]

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Scofflaw

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This month Scofflaw bar manager Luke DeYoung and partner Danny Shapiro introduced a slate of fall elixirs to the beloved Logan Square bar. Bargoers can try drinks like the Swizzle 26 (tequila, falernum, Cynar, lime, honey, and spicy Fee Brothers old fashioned bitters), and a seasonal Negroni riff called Other Limits (Citadelle gin, Lustau Vermut Rouge, Amaro Lucano, Amaro Novasalus).

3201 W Armitage Ave, Chicago, IL 60647
(773) 252-9700
(773) 252-9700
Cocktails at Scofflaw.
Jude Goergen

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The J. Parker

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Hotel Lincoln’s rooftop bar The J. Parker, by Lincoln Park, introduced its fall cocktail menu this month. The theme is “The Darkside of Paradise,” and all drinks are named after tourist destinations reputed for having a dark or haunted past. Beverage director Jonathan Kahn is responsible for the list, which includes the 1140 Royal (rum, pistachio, chai, vanilla, pumpkin, and dark chocolate), and Forbidden City (apple-infused Scotch, oaked apple brandy, honey, lemon, ginger, and lapsang souchong tea).

1816 N Clark St, Chicago, IL 60614
(312) 254-4747
(312) 254-4747
The J. Parker
Eric Kleinberg

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The Violet Hour

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Requisite Chicago drinking haunt The Violet Hour is a cool-weather cocktail haven with candlelight and a flickering fireplace. Head mixologist Toby Maloney and managing partner Eden Laurin’s fall list rolled out this month, with season-appropriate drams such as Rudy’s Revenge, a fall take on a classic Moscow mule (Amaro Nardini, Abita Brewing Company’s Munich-style Amber ale, rye, house-made ginger syrup and orange bitters) and For Good Measure, a fall-focused, low-ABV take on sangria (Carpano Antica vermouth, port, red wine syrup, lemon, and muddled orange peel).

1520 N Damen Ave, Chicago, IL 60622
(773) 252-1500
(773) 252-1500
Inside The Violet Hour
The Violet Hour [Official Photo]

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Drumbar

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For fall-flavored, sky-high cocktails, Drumbar, the speakeasy-style bar atop Streeterville’s Raffaello Hotel, has multiple elevated options. Rich in seasonal ingredients, the Concord Grape Cobbler (vodka, sherry, nocino, concord grape, lemon) or Tequila Pumpkin Seed Mia Mai (tequila, salted pumpkin seed orgeat, hoja santa, spiced tepache, lime) offer boozy fall flavors like few others.

201 E Delaware Pl, Chicago, IL 60611
(312) 933-4805
(312) 933-4805
Drumbar’s Tequila Pumpkin Seed Mai Tai
Drumbar/Facebook

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Split-Rail

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In tandem with that menu switch to focus on fried chicken, last month West Town’s Split-Rail inaugurated a new beverage list curated by general manager Michelle Szot and bar manager Brenna Washow. Look for tipples like Eight Dolla Holla (bourbon, dry vermouth, spiced demerara, and orange bitters) and Stay Out Of The Forest, inspired by true crime/comedy podcast My Favorite Murder (Vikre spruce gin, Zirbenz Alpine liqueur, grapefruit, and lime).

2500 W Chicago Ave, Chicago, IL 60622
(773) 697-4413
(773) 697-4413
Split-Rail’s bar.
Split-Rail [Official Photo]

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Three Dots and a Dash

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River North tiki den Three Dots and a Dash launched its new fall menu with beverage director Kevin Beary’s libations like Suffering Bastard (gin, Calvados, eau de vie de cidre, lime, ginger, sasparilla) and Quincy With The Good Pear (aged cachaca, Martinique rhum agricole, lime, pineapple, quince, pear)

435 N Clark St, Chicago, IL 60654
(312) 610-4220
(312) 610-4220
Three Dots’ Suffering Bastard cocktail.
Jeff Marini

Also featured in:

Aba

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Chef CJ Jacobson’s smash summer hit Aba has changed over its bar menu to include a number of fall intoxicants. The lush River North eatery and rooftop terrace has new drinks like the Hyrbrid Sour (Chairman’s Reserve, rye, Suze, maple, orange, lemon), and Aged By Air (bourbon, Cardamaro, East India sherry, walnut, arak).

302 N Green St 3rd floor, Chicago, IL 60607
(773) 645-1400
(773) 645-1400
Aba’s bar.
Christina Slaton

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Raised, an Urban Rooftop Bar

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Last month rooftop bar Raised in The Loop kicked of a fresh slate of fall tipples. Barman William Nykaza is behind the new additions, like Wild Ones (tequila, yellow Chartreuse, allspice, egg white, lemon, and honey), and Espresso Yourself (vodka, espresso, cream, almond liqueur, and chocolate-almond sea salt syrup).

1 W Wacker Dr, Chicago, IL 60601
(312) 795-3444
(312) 795-3444
Inside Raised
Raised [Official Photo]

Also featured in:

The Loyalist

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Chef John Shields’ American bistro The Loyalist debuted its fall cocktail menu this month, helmed by lead bartender Kirill Kuznetsoff. Expect to find drinks like Birch Please (homemade birch syrup, shochu, vermouth, lemon and soda), and The Doctor’s Orders (pine syrup plus bourbon, Strega, scotch, lemon and honey).

177 N Ada St #001, Chicago, IL 60607
(773) 913-3774
(773) 913-3774
The Loyalist’s bar.
The Loyalist

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Tinker To Evers

3473 N Clark St, Chicago, IL 60657

The first cocktail menu from newbie basement bar Tinker To Evers, which debuted below Detroit-style pizzeria Union Full Board earlier this month in Wrigleyville, entirely channels fall. Here one will find a bevy of fall-forward flavors, like sherry, thyme liquor, walnut, and celery bitters. Try tipples like Leche Di Tigre (Nola Chicory Liquor, horchata, and walnut bitters), and Mr. Sunshine (Bols Genever gin, thyme liqueur, lemon, and Angostura bitters).

3473 N Clark St, Chicago, IL 60657
(773) 248-9001
(773) 248-9001
Inside Tinker To Evers
Tinker To Evers [Official Photo]

Longman & Eagle

2657 N Kedzie Ave, Chicago, IL 60647

Logan Square fixture Longman & Eagle’s seasonal fall drinks list is out. Devised by the gastropub’s bar team, lead by beverage director Tony Correale and bar managers Nathan Case-McDonald and Jake Dean, come in for drinks like Clock Without Hands (Very Old Barton Bonded, Amer Gingembre, genmaicha green tea, yuzu honey, lemon) and The Kentucky Kick-start (Maker’s Mark Private Select Red Top, Dark Matter coffee, Cap Corse Blanc, honey, lemon).

2657 N Kedzie Ave, Chicago, IL 60647
(773) 276-7110
(773) 276-7110
Longman & Eagle
Clayton Hauck

Billy Sunday

3143 W Logan Blvd, Chicago, IL 60647

Beloved Logan Square drinking den Billy Sunday launched its fall libation list with standouts by bar manager Stephanie Andrews including a play on Starbucks’ PSL reworked into an autumnal milk punch served in a pumpkin (rum, bourbon, pumpkin pie spice, rooibos tea, and lemon) for four to six imbibers, and Papa Don’t Peach (whiskey, smoked peaches, fig wood, lemon, and egg white), served in a Russian doll.

3143 W Logan Blvd, Chicago, IL 60647
(773) 661-2485
(773) 661-2485
Billy Sunday’s Papa Don’t Peach cocktail.
Billy Sunday [Official Photo]

Quiote/Todos Santos

2456 N California Ave, Chicago, IL 60647

Chicago’s most expansive collection of small-production mezcal lives at Todos Santos, the subterranean bar below Logan Square’s Mexican eatery, Quiote. And while smoky mezcal itself makes for a warming seasonal sipper, in September barman Jay Schroeder’s new drinks list rolled out, with creations like Life During Wartime (apricot cordial, Scotch, mezcal, house-made pasilla chili-rooibos syrup, and bitter orange juice) and Check My SoundCloud (sotol, chili liqueur, absinthe, lemon, canola, and hoja santa salt).

2456 N California Ave, Chicago, IL 60647
(312) 878-8571
(312) 878-8571
Todos Santos’ Life During Wartime
Quiote/Todos Santos [Official Photo]

Scofflaw

3201 W Armitage Ave, Chicago, IL 60647

This month Scofflaw bar manager Luke DeYoung and partner Danny Shapiro introduced a slate of fall elixirs to the beloved Logan Square bar. Bargoers can try drinks like the Swizzle 26 (tequila, falernum, Cynar, lime, honey, and spicy Fee Brothers old fashioned bitters), and a seasonal Negroni riff called Other Limits (Citadelle gin, Lustau Vermut Rouge, Amaro Lucano, Amaro Novasalus).

3201 W Armitage Ave, Chicago, IL 60647
(773) 252-9700
(773) 252-9700
Cocktails at Scofflaw.
Jude Goergen

The J. Parker

1816 N Clark St, Chicago, IL 60614

Hotel Lincoln’s rooftop bar The J. Parker, by Lincoln Park, introduced its fall cocktail menu this month. The theme is “The Darkside of Paradise,” and all drinks are named after tourist destinations reputed for having a dark or haunted past. Beverage director Jonathan Kahn is responsible for the list, which includes the 1140 Royal (rum, pistachio, chai, vanilla, pumpkin, and dark chocolate), and Forbidden City (apple-infused Scotch, oaked apple brandy, honey, lemon, ginger, and lapsang souchong tea).

1816 N Clark St, Chicago, IL 60614
(312) 254-4747
(312) 254-4747
The J. Parker
Eric Kleinberg

The Violet Hour

1520 N Damen Ave, Chicago, IL 60622

Requisite Chicago drinking haunt The Violet Hour is a cool-weather cocktail haven with candlelight and a flickering fireplace. Head mixologist Toby Maloney and managing partner Eden Laurin’s fall list rolled out this month, with season-appropriate drams such as Rudy’s Revenge, a fall take on a classic Moscow mule (Amaro Nardini, Abita Brewing Company’s Munich-style Amber ale, rye, house-made ginger syrup and orange bitters) and For Good Measure, a fall-focused, low-ABV take on sangria (Carpano Antica vermouth, port, red wine syrup, lemon, and muddled orange peel).

1520 N Damen Ave, Chicago, IL 60622
(773) 252-1500
(773) 252-1500
Inside The Violet Hour
The Violet Hour [Official Photo]

Drumbar

201 E Delaware Pl, Chicago, IL 60611

For fall-flavored, sky-high cocktails, Drumbar, the speakeasy-style bar atop Streeterville’s Raffaello Hotel, has multiple elevated options. Rich in seasonal ingredients, the Concord Grape Cobbler (vodka, sherry, nocino, concord grape, lemon) or Tequila Pumpkin Seed Mia Mai (tequila, salted pumpkin seed orgeat, hoja santa, spiced tepache, lime) offer boozy fall flavors like few others.

201 E Delaware Pl, Chicago, IL 60611
(312) 933-4805
(312) 933-4805
Drumbar’s Tequila Pumpkin Seed Mai Tai
Drumbar/Facebook

Split-Rail

2500 W Chicago Ave, Chicago, IL 60622

In tandem with that menu switch to focus on fried chicken, last month West Town’s Split-Rail inaugurated a new beverage list curated by general manager Michelle Szot and bar manager Brenna Washow. Look for tipples like Eight Dolla Holla (bourbon, dry vermouth, spiced demerara, and orange bitters) and Stay Out Of The Forest, inspired by true crime/comedy podcast My Favorite Murder (Vikre spruce gin, Zirbenz Alpine liqueur, grapefruit, and lime).

2500 W Chicago Ave, Chicago, IL 60622
(773) 697-4413
(773) 697-4413
Split-Rail’s bar.
Split-Rail [Official Photo]

Three Dots and a Dash

435 N Clark St, Chicago, IL 60654

River North tiki den Three Dots and a Dash launched its new fall menu with beverage director Kevin Beary’s libations like Suffering Bastard (gin, Calvados, eau de vie de cidre, lime, ginger, sasparilla) and Quincy With The Good Pear (aged cachaca, Martinique rhum agricole, lime, pineapple, quince, pear)

435 N Clark St, Chicago, IL 60654
(312) 610-4220
(312) 610-4220
Three Dots’ Suffering Bastard cocktail.
Jeff Marini

Aba

302 N Green St 3rd floor, Chicago, IL 60607

Chef CJ Jacobson’s smash summer hit Aba has changed over its bar menu to include a number of fall intoxicants. The lush River North eatery and rooftop terrace has new drinks like the Hyrbrid Sour (Chairman’s Reserve, rye, Suze, maple, orange, lemon), and Aged By Air (bourbon, Cardamaro, East India sherry, walnut, arak).

302 N Green St 3rd floor, Chicago, IL 60607
(773) 645-1400
(773) 645-1400
Aba’s bar.
Christina Slaton

Raised, an Urban Rooftop Bar

1 W Wacker Dr, Chicago, IL 60601

Last month rooftop bar Raised in The Loop kicked of a fresh slate of fall tipples. Barman William Nykaza is behind the new additions, like Wild Ones (tequila, yellow Chartreuse, allspice, egg white, lemon, and honey), and Espresso Yourself (vodka, espresso, cream, almond liqueur, and chocolate-almond sea salt syrup).

1 W Wacker Dr, Chicago, IL 60601
(312) 795-3444
(312) 795-3444
Inside Raised
Raised [Official Photo]

The Loyalist

177 N Ada St #001, Chicago, IL 60607

Chef John Shields’ American bistro The Loyalist debuted its fall cocktail menu this month, helmed by lead bartender Kirill Kuznetsoff. Expect to find drinks like Birch Please (homemade birch syrup, shochu, vermouth, lemon and soda), and The Doctor’s Orders (pine syrup plus bourbon, Strega, scotch, lemon and honey).

177 N Ada St #001, Chicago, IL 60607
(773) 913-3774
(773) 913-3774
The Loyalist’s bar.
The Loyalist

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