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Two wooden glasses that look like wine barrels with ice sticking out. — Billy Sunday’s Tell No Tails

20 Fantastic Fall Cocktails to Try in Chicago Now

From caramel apple poptails to corn cobblers

by Kat Odell Oct 11, 2019, 1:15pm CDT

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Billy Sunday’s Tell No Tails

| Jaysen Goranson

by Kat Odell Oct 11, 2019, 1:15pm CDT

As bright and juicy summer ingredients fade out of season, warm fall flavors set into Chicago bars. That means corn, 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 anti-take on the popular drink.

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 liquid form.

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Sunda

River North’s modern Asian eatery Sunda is celebrating fall with “peared sake.” Beverage director Nahm Kim blends pear vodka with sparkling sake, pineapple juice, ginger syrup, then garnishes the libation with a Saigon cinnamon rim. Says Kim: “Sparkling sake was not a popular drink when Sunda opened in 2009, so creating a sparkling sake cocktail was one way Sunda introduced this sake to their guests.”

110 W Illinois St, Chicago, IL 60654

Visit Website

A short clear glass containing a yellow-colored cocktail garnished with a piece of dried pineapple. — Sunda’s Peared Sake

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etta

Over at etta, Wicker Park’s new American number, the bar team has schemed a tiki-inspired fall cocktail that they say, “takes you to the beach in Barbados, while remind[ing] you that your friends back in Chicago are all wearing sweatshirts.” “Team builder” calls for Pimm’s, Jamaican rum, china-china, lime, mango, mint, and a tres leches orgeat syrup that’s flavored with cinnamon and allspice.

1840 W North Ave, Chicago, IL 60622

Visit Website

A tall clear glass filled with a milky, brown-colored cocktail. — Etta’s Team Builder

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Daisies

There’s perhaps no better way to wrap up summer then by savoring the end of fresh corn season. The bar team at new American restaurant Daisies in Logan Square came up with “corn cobbler.” The drink—served in a coupe glass—incorporates a blend of rums, saffron liqueur, roasted corn, apple cider vinegar, and tarragon.

2523 N Milwaukee Ave, Chicago, IL 60647

Visit Website

A coupe glass filled with a orange-yellow cocktail. — Daisies’ Corn Cobbler

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Onward Chicago

Vicente Romero, cocktail director and assistant general manager at Onward—the new American Rogers Park restaurant from the former owner of now-shuttered, three-Michelin-starred Grace—is responsible for “apple pie butterfly.” This fall-forward tipple embraces the season with apple-cinnamon syrup, rum, Cocchi Americano, lemon juice, and a few drops of absinthe.

6580 N Sheridan Rd, Chicago, IL 60626

Visit Website

A medium-sized glass filled with a red-colored cocktail and a lime garnish. — Apple Pie Butterfly

IO Godfrey Rooftop Lounge

The bar team at River North rooftop lounge I|O Godfrey is experimenting with a slate of ingredient-intensive drinks they’re calling “kitchen cocktails.” One such new libation is the Godfrey Toddy, an infused drink made in a siphon coffee maker. The concoction is composed of whiskey, honey, and water, plus cinnamon sticks, star anise, lemon peel, vanilla bean, clove, lemongrass, and rosemary.

Open in Google Maps

127 W Huron St, Chicago, IL 60654

Visit Website

A siphon coffee maker filled with a yellow liquid and two glasses holding that same yellow liquid. — IO Godfrey’s Godfrey Toddy

Also featured in:

The Delta

Partner and beverage director Adam Kamin from Wicker Park cocktail bar the Delta is the man behind “what a pear.” He blends the fall fruit with a 10-year-aged pear brandy, vanilla, ginger, lime, and orange bitters.

Open in Google Maps

1745 W North Ave, Chicago, IL 60622

Visit Website

A rocks glass filled with a yellow drink. — The Delta’s What a Pear

Also featured in:

Wicker Park’s Best Restaurants

The Publican

Fulton Market gastropub the Publican just this month added “the golden hour” to its drinks lineup. Inspired by autumn and a new saffron spirit on they market, beverage manager Melissa Romanos blends gin, Apologue Saffron Liqueur, Dolin Genepy, chile-cardamom honey, and lemon juice. Says Romanos, “this is perfect for fall because all the spices call for cooler nights, but it’s still refreshing enough for those warmer days.”

837 W Fulton Market, Chicago, IL 60607

Visit Website

A short white tea cup holding a yellow-colored drink. — The Publican’s Golden Hour

Also featured in:

Dusek's Board & Beer

Two weeks ago, beverage director Rob Boyd added “here & there” to Michelin-starred gastropub Dusek’s Board and Beer’s cocktail menu. Likewise inspired by new saffron spirit Apologue Saffron Liqueur, he adds the liqeuor plus mezcal, lime juice, pomegranate-turmeric syrup, mole bitters, and an egg white. Per Boyd, “This cocktail blends the traditional autumnal flavors of home—such as pomegranate, ginger, and golden raisins—with the faraway flavors of mezcal and mole found in Oaxaca.”

1227 W 18th St, Chicago, IL 60608

Visit Website

A coupe glass positioned on top of a menu, holding a brown-colored drink topped with egg white foam. — Dusek’s Board and Beer’s Here & There

Also featured in:

Revival Food Hall

This month, bartender Clare Murrell introduced a new fall-leaning cocktail to Revival Food Hall’s new bar menu that’s inspired by turn-of-the-century skyscrapers in downtown Chicago. Murell explains that, “the Manhattan Building has a caramel-colored facade and quirky or nutty design features like smiling gargoyles and stylized lettering.” She turned those aesthetics into a Manhattan riff that offers notes of hazelnut, almond, chocolate, and subtle spice. “Manhattan Building” calls for hazelnut-almond butter-infused rye, coffee-infused Cynar, red vermouth, amontillado sherry, and Madeira.

125 S Clark St, Chicago, IL 60603

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A clear glass filled with a brown cocktail . — Revival Food Hall’s Manhattan Building

Also featured in:

RAISED | An Urban Rooftop Bar

Earlier this month, bartender Rachel Johnson over at Raised—the American restaurant and rooftop bar overlooking the Chicago River— decided to rethink one of the most classic fall treats: caramel apples. Her “caramel apple poptail” calls for Fratello Hazelnut liqueur, Ramazzotti, apple cider, and honey.

1 W Wacker Dr, Chicago, IL 60601

Visit Website

A hand holding a yellow, triangle-shaped ice pop. — Raised’s Caramel Apple Poptail

Also featured in:

RPM Steak

Perpetually buzzy River North steak spot RPM Steak has a new fall intoxicant on the cocktail list as of this month. Barman Joseph Lapi conceived of this seasonal gin and tonic titled “the M gin & tonic,” and it calls for Monkey 47 gin, apple brandy, riesling, lemongrass, cranberries and Fever-Tree tonic. Says Lapi, “While many gin and tonics call for lime, we use these heartier fall ingredients to help stretch the seasons.”

66 W Kinzie St, Chicago, IL 60654

Visit Website

A silver tray holding assorted spirits and a wine glass filled with a gin and tonic. — “M” Gin & Tonic

Also featured in:

Petterino's

Who says a Spritz can only be sipped in the summer? The Loop Italian haunt Petterino’s believes otherwise. Enter, “the Harvest Spritz,” by bartender Blake Dressel, who explains that his drink contains “a balanced mix of bitter orange amaro, the crisp semi-dry Right Bee Cider and spicy ginger beer.” On the menu as of this month, the cocktail comes in a wine glass filled with ice, garnished with an apple slice and orange peel twist.

150 N Dearborn St, Chicago, IL 60601

Visit Website

A wine glass containing a brown cocktail. — Petterino’s Harvest Spritz

Also featured in:

13 Great Restaurants in Chicago’s Theater District For Dinner and a Show

Osteria Via Stato

River North’s Osteria Via Stato is feeling fall via its “farmer’s mule.” Bartender Dan Kurtzman added the drink earlier this month, offering a blend of local pears, cinnamon, vodka, and ginger beer.

620 N State St, Chicago, IL 60654

Visit Website

A rock glass containing a light brown-colored cocktail. — Osteria Via Stato’s Farmer’s Mule

Also featured in:

Machine: Engineered Dining & Drink

Beverage Director Aneka Saxon at Wicker Park’s American addition Machine drew inspiration from the humble carrot with her new vegetal cocktail, “eye don’t carrot all.” Her anti-pumpkin spice libation calls for carrot, gin, lemon, cumin, turmeric, ginger, red pepper, coriander, orange, and it’s served with a frozen watermelon shard in place of ice cubes. Says Saxon, “the frozen watermelon shard serves to add flavor while also keeping the drink cold without diluting the taste.”

1846 W Division St, Chicago, IL 60622

Visit Website

A Collins glass containing a carrot orange-hued drink with coriander leaves sticking out. — Machine’s Eye Don’t Carrot All

Galit

Newbie Israeli hotspot Galit in Lincoln Park is leaning into fall via “it’s muhammara” by beverage director Olivia Duncan. Her drink calls for rum, tequila, red bell pepper, caraway, and walnut. Duncan explains, “this drink is a split base of rum and tequila—the spirits play really well with the ... bright fresh pepper and also the comfort spice of caraway with a touch of walnut.”

2429 N Lincoln Ave, Chicago, IL 60614

Visit Website

A red cocktail in a coupe glass. — Galit’s It’s Muhammara

Also featured in:

The Violet Hour

This week, decorated Wicker Park cocktail cabin the Violet Hour introduce “London frog.” To make the drink, bartender Lisa Greene blends vodka, Amaro de Montenegro, Italicus Bergamotto, Earl Grey syrup, lemon juice, and egg white. Lisa Greene says that her libation is “a boozy twist on a London Fog latte—the cocktail drinks like the coffee shop classic, complete with foamy nose, notes of lemon and cold weather bergamot orange.”

1520 N Damen Ave, Chicago, IL 60622

Visit Website

A silver tray positioned by a fire place with a brown drink in a clear glass. — The Violet Hour’s London Fog

Also featured in:

Lone Wolf

“Old dog, new tricks” by general manager Kristina Magro represents Lone Wolf‘s nod to fall. Served in an old-school juice box, the dram involves tequila, sake, Michigan apple cider, lemon juice, and honey.

806 W Randolph St, Chicago, IL 60607

Visit Website

A small, square, turquoise juice box. — Lone Wolf’s Old Dog New Tricks

Also featured in:

Yūgen Restaurant

Grace replacement Yūgen is offering a sort of Japanese-style toddy. “The boilerman” includes plum whiskey, oolong tea, cinnamon, ginger, black peppercorn, and star anise.

Open in Google Maps

652 W Randolph St, Chicago, IL 60661

Visit Website

A wooden cup with a tea bag sticking out. — Yūgen’s The Boilerman

Also featured in:

Young American

Logan Square cocktail bar Young American is mixing the #4 for fall. On the menu as of this month, “the drink is a riff on a Lion’s Tail, with wonderful fall spice from the cinnamon and allspice dram,” explains drink creator Wade McElroy. Think amontillado and fino sherry, bonded bourbon, allspice dram, concord grape grenadine, and lime juice.

2545 N Kedzie Ave, Chicago, IL 60647

Visit Website

A beige-colored cocktail in a coupe glass, sitting on a bar. — Young American’s #4

Also featured in:

Billy Sunday

Beloved Logan Square lair Billy Sunday presents “tell no tails,” inspired by the late-summer-to-late-fall seasonality of passion fruit. Designed by bartender Jeremy Barrett, the drink calls for scotch, aged agricole rhum, ginger amaro, passion fruit, lime juice, and cacao.

3143 W Logan Blvd, Chicago, IL 60647

Visit Website

Two wooden glasses that look like wine barrels with ice sticking out. — Billy Sunday’s Tell No Tails

Also featured in:

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Sunda

110 W Illinois St, Chicago, IL 60654

River North’s modern Asian eatery Sunda is celebrating fall with “peared sake.” Beverage director Nahm Kim blends pear vodka with sparkling sake, pineapple juice, ginger syrup, then garnishes the libation with a Saigon cinnamon rim. Says Kim: “Sparkling sake was not a popular drink when Sunda opened in 2009, so creating a sparkling sake cocktail was one way Sunda introduced this sake to their guests.”

110 W Illinois St, Chicago, IL 60654

Visit Website

A short clear glass containing a yellow-colored cocktail garnished with a piece of dried pineapple. — Sunda’s Peared Sake

etta

1840 W North Ave, Chicago, IL 60622

Over at etta, Wicker Park’s new American number, the bar team has schemed a tiki-inspired fall cocktail that they say, “takes you to the beach in Barbados, while remind[ing] you that your friends back in Chicago are all wearing sweatshirts.” “Team builder” calls for Pimm’s, Jamaican rum, china-china, lime, mango, mint, and a tres leches orgeat syrup that’s flavored with cinnamon and allspice.

1840 W North Ave, Chicago, IL 60622

Visit Website

A tall clear glass filled with a milky, brown-colored cocktail. — Etta’s Team Builder

Daisies

2523 N Milwaukee Ave, Chicago, IL 60647

There’s perhaps no better way to wrap up summer then by savoring the end of fresh corn season. The bar team at new American restaurant Daisies in Logan Square came up with “corn cobbler.” The drink—served in a coupe glass—incorporates a blend of rums, saffron liqueur, roasted corn, apple cider vinegar, and tarragon.

2523 N Milwaukee Ave, Chicago, IL 60647

Visit Website

A coupe glass filled with a orange-yellow cocktail. — Daisies’ Corn Cobbler

Onward Chicago

6580 N Sheridan Rd, Chicago, IL 60626

Vicente Romero, cocktail director and assistant general manager at Onward—the new American Rogers Park restaurant from the former owner of now-shuttered, three-Michelin-starred Grace—is responsible for “apple pie butterfly.” This fall-forward tipple embraces the season with apple-cinnamon syrup, rum, Cocchi Americano, lemon juice, and a few drops of absinthe.

6580 N Sheridan Rd, Chicago, IL 60626

Visit Website

A medium-sized glass filled with a red-colored cocktail and a lime garnish. — Apple Pie Butterfly

IO Godfrey Rooftop Lounge

127 W Huron St, Chicago, IL 60654

The bar team at River North rooftop lounge I|O Godfrey is experimenting with a slate of ingredient-intensive drinks they’re calling “kitchen cocktails.” One such new libation is the Godfrey Toddy, an infused drink made in a siphon coffee maker. The concoction is composed of whiskey, honey, and water, plus cinnamon sticks, star anise, lemon peel, vanilla bean, clove, lemongrass, and rosemary.

Open in Google Maps

127 W Huron St, Chicago, IL 60654

Visit Website

A siphon coffee maker filled with a yellow liquid and two glasses holding that same yellow liquid. — IO Godfrey’s Godfrey Toddy

The Delta

1745 W North Ave, Chicago, IL 60622

Partner and beverage director Adam Kamin from Wicker Park cocktail bar the Delta is the man behind “what a pear.” He blends the fall fruit with a 10-year-aged pear brandy, vanilla, ginger, lime, and orange bitters.

Open in Google Maps

1745 W North Ave, Chicago, IL 60622

Visit Website

A rocks glass filled with a yellow drink. — The Delta’s What a Pear

The Publican

837 W Fulton Market, Chicago, IL 60607

Fulton Market gastropub the Publican just this month added “the golden hour” to its drinks lineup. Inspired by autumn and a new saffron spirit on they market, beverage manager Melissa Romanos blends gin, Apologue Saffron Liqueur, Dolin Genepy, chile-cardamom honey, and lemon juice. Says Romanos, “this is perfect for fall because all the spices call for cooler nights, but it’s still refreshing enough for those warmer days.”

837 W Fulton Market, Chicago, IL 60607

Visit Website

A short white tea cup holding a yellow-colored drink. — The Publican’s Golden Hour

Dusek's Board & Beer

1227 W 18th St, Chicago, IL 60608

Two weeks ago, beverage director Rob Boyd added “here & there” to Michelin-starred gastropub Dusek’s Board and Beer’s cocktail menu. Likewise inspired by new saffron spirit Apologue Saffron Liqueur, he adds the liqeuor plus mezcal, lime juice, pomegranate-turmeric syrup, mole bitters, and an egg white. Per Boyd, “This cocktail blends the traditional autumnal flavors of home—such as pomegranate, ginger, and golden raisins—with the faraway flavors of mezcal and mole found in Oaxaca.”

1227 W 18th St, Chicago, IL 60608

Visit Website

A coupe glass positioned on top of a menu, holding a brown-colored drink topped with egg white foam. — Dusek’s Board and Beer’s Here & There

Revival Food Hall

125 S Clark St, Chicago, IL 60603

This month, bartender Clare Murrell introduced a new fall-leaning cocktail to Revival Food Hall’s new bar menu that’s inspired by turn-of-the-century skyscrapers in downtown Chicago. Murell explains that, “the Manhattan Building has a caramel-colored facade and quirky or nutty design features like smiling gargoyles and stylized lettering.” She turned those aesthetics into a Manhattan riff that offers notes of hazelnut, almond, chocolate, and subtle spice. “Manhattan Building” calls for hazelnut-almond butter-infused rye, coffee-infused Cynar, red vermouth, amontillado sherry, and Madeira.

125 S Clark St, Chicago, IL 60603

Visit Website

A clear glass filled with a brown cocktail . — Revival Food Hall’s Manhattan Building

RAISED | An Urban Rooftop Bar

1 W Wacker Dr, Chicago, IL 60601

Earlier this month, bartender Rachel Johnson over at Raised—the American restaurant and rooftop bar overlooking the Chicago River— decided to rethink one of the most classic fall treats: caramel apples. Her “caramel apple poptail” calls for Fratello Hazelnut liqueur, Ramazzotti, apple cider, and honey.

1 W Wacker Dr, Chicago, IL 60601

Visit Website

A hand holding a yellow, triangle-shaped ice pop. — Raised’s Caramel Apple Poptail

RPM Steak

66 W Kinzie St, Chicago, IL 60654

Perpetually buzzy River North steak spot RPM Steak has a new fall intoxicant on the cocktail list as of this month. Barman Joseph Lapi conceived of this seasonal gin and tonic titled “the M gin & tonic,” and it calls for Monkey 47 gin, apple brandy, riesling, lemongrass, cranberries and Fever-Tree tonic. Says Lapi, “While many gin and tonics call for lime, we use these heartier fall ingredients to help stretch the seasons.”

66 W Kinzie St, Chicago, IL 60654

Visit Website

A silver tray holding assorted spirits and a wine glass filled with a gin and tonic. — “M” Gin & Tonic

Petterino's

150 N Dearborn St, Chicago, IL 60601

Who says a Spritz can only be sipped in the summer? The Loop Italian haunt Petterino’s believes otherwise. Enter, “the Harvest Spritz,” by bartender Blake Dressel, who explains that his drink contains “a balanced mix of bitter orange amaro, the crisp semi-dry Right Bee Cider and spicy ginger beer.” On the menu as of this month, the cocktail comes in a wine glass filled with ice, garnished with an apple slice and orange peel twist.

150 N Dearborn St, Chicago, IL 60601

Visit Website

A wine glass containing a brown cocktail. — Petterino’s Harvest Spritz

Osteria Via Stato

620 N State St, Chicago, IL 60654

River North’s Osteria Via Stato is feeling fall via its “farmer’s mule.” Bartender Dan Kurtzman added the drink earlier this month, offering a blend of local pears, cinnamon, vodka, and ginger beer.

620 N State St, Chicago, IL 60654

Visit Website

A rock glass containing a light brown-colored cocktail. — Osteria Via Stato’s Farmer’s Mule

Machine: Engineered Dining & Drink

1846 W Division St, Chicago, IL 60622

Beverage Director Aneka Saxon at Wicker Park’s American addition Machine drew inspiration from the humble carrot with her new vegetal cocktail, “eye don’t carrot all.” Her anti-pumpkin spice libation calls for carrot, gin, lemon, cumin, turmeric, ginger, red pepper, coriander, orange, and it’s served with a frozen watermelon shard in place of ice cubes. Says Saxon, “the frozen watermelon shard serves to add flavor while also keeping the drink cold without diluting the taste.”

1846 W Division St, Chicago, IL 60622

Visit Website

A Collins glass containing a carrot orange-hued drink with coriander leaves sticking out. — Machine’s Eye Don’t Carrot All

Galit

2429 N Lincoln Ave, Chicago, IL 60614

Newbie Israeli hotspot Galit in Lincoln Park is leaning into fall via “it’s muhammara” by beverage director Olivia Duncan. Her drink calls for rum, tequila, red bell pepper, caraway, and walnut. Duncan explains, “this drink is a split base of rum and tequila—the spirits play really well with the ... bright fresh pepper and also the comfort spice of caraway with a touch of walnut.”

2429 N Lincoln Ave, Chicago, IL 60614

Visit Website

A red cocktail in a coupe glass. — Galit’s It’s Muhammara

Related Maps

The Violet Hour

1520 N Damen Ave, Chicago, IL 60622

This week, decorated Wicker Park cocktail cabin the Violet Hour introduce “London frog.” To make the drink, bartender Lisa Greene blends vodka, Amaro de Montenegro, Italicus Bergamotto, Earl Grey syrup, lemon juice, and egg white. Lisa Greene says that her libation is “a boozy twist on a London Fog latte—the cocktail drinks like the coffee shop classic, complete with foamy nose, notes of lemon and cold weather bergamot orange.”

1520 N Damen Ave, Chicago, IL 60622

Visit Website

A silver tray positioned by a fire place with a brown drink in a clear glass. — The Violet Hour’s London Fog

Lone Wolf

806 W Randolph St, Chicago, IL 60607

“Old dog, new tricks” by general manager Kristina Magro represents Lone Wolf‘s nod to fall. Served in an old-school juice box, the dram involves tequila, sake, Michigan apple cider, lemon juice, and honey.

806 W Randolph St, Chicago, IL 60607

Visit Website

A small, square, turquoise juice box. — Lone Wolf’s Old Dog New Tricks

Yūgen Restaurant

652 W Randolph St, Chicago, IL 60661

Grace replacement Yūgen is offering a sort of Japanese-style toddy. “The boilerman” includes plum whiskey, oolong tea, cinnamon, ginger, black peppercorn, and star anise.

Open in Google Maps

652 W Randolph St, Chicago, IL 60661

Visit Website

A wooden cup with a tea bag sticking out. — Yūgen’s The Boilerman

Young American

2545 N Kedzie Ave, Chicago, IL 60647

Logan Square cocktail bar Young American is mixing the #4 for fall. On the menu as of this month, “the drink is a riff on a Lion’s Tail, with wonderful fall spice from the cinnamon and allspice dram,” explains drink creator Wade McElroy. Think amontillado and fino sherry, bonded bourbon, allspice dram, concord grape grenadine, and lime juice.

2545 N Kedzie Ave, Chicago, IL 60647

Visit Website

A beige-colored cocktail in a coupe glass, sitting on a bar. — Young American’s #4

Billy Sunday

3143 W Logan Blvd, Chicago, IL 60647

Beloved Logan Square lair Billy Sunday presents “tell no tails,” inspired by the late-summer-to-late-fall seasonality of passion fruit. Designed by bartender Jeremy Barrett, the drink calls for scotch, aged agricole rhum, ginger amaro, passion fruit, lime juice, and cacao.

3143 W Logan Blvd, Chicago, IL 60647

Visit Website

Two wooden glasses that look like wine barrels with ice sticking out. — Billy Sunday’s Tell No Tails

Related Maps