Despite what Cinderella’s fairy godmother said, we wouldn’t mind one bit if all summer beverages turned into pumpkins. And we’re not talking PSLs. No, we’ve got something better—booze. Say hello to October and welcome the fine flavors its fruits bear. From pumpkin, apple and dark fruit to chocolate, smoky, savory and spiced, Chicago’s bars are helping keep your glasses full with the essence of fall. Check out these 15 cocktails and get your fall fix, ya pumpkin heads.
PUMPKIN
Momma D’s Pumpkin Pie ($10) at The Promontory
5311 S. Lake Park Ave. 312-801-2100
Choosing just one cocktail from the Hyde Park bar’s fall menu wasn’t easy—until we saw the pumpkin concoction with our 2015 Best Bartender finalist Dianna Sanders’ name all over it (literally, kind of). This dessert in a glass makes pumpkin pie on a plate seem boring. Pisco is fat-washed with brown butter in-house (butter is added to the spirit and the concoction is chilled until the butter solidifies enough to be skimmed off, leaving the flavor behind) and mixed with housemade pumpkin soda, graham-cracker syrup and maple whip. Also noteworthy: the rum-raisin old fashioned and the rum-based Scary Spice cocktail with pumpkin butter.
Winter is Coming ($11) at Lillie’s Q
1856 W. North Ave. 773-772-5500
Pumpkin, great. Pumpkin and gin, better! Pumpkin, gin AND apple? What is this autumn magic? Stop by the Wicker Park meat house next week for this gin cocktail with a housemade pumpkin reduction and lemon juice topped with Vander Mill’s Totally Roasted hard cider and a lemon peel.
APPLE
Wassail ($8) at Pub Royale
2049 W. Division St. 773-661-6874
Go a-wassailing to this British-Indian-inspired Wicker Park spot for a warm treat made with an apple blend—cored and baked with demerara sugar, citrus juice, clove and allspice—cider, Madeira and port wines garnished with grated nutmeg and an orange swath.
The Harvest ($13) at Celeste
111 W. Hubbard St. 312-828-9000
Two words: apple butter. This brandy cocktail at the River North bar has it, and the only thing that would make it better is a cinnamon stick. But wait, it has that too!
SPICED
Ghost Town Fizz ($12) at The Dawson
730 W. Grand Ave. 312-243-8955
As always, Harrison Ginsberg (another 2015 Best Bartender participant) and his team at the West Town bar-restaurant deliver on the details, and this fall’s cocktail selection, launching Oct. 15, doesn’t disappoint (there’s even one with gold-painted lemon garnishes). We recommend this pisco- and vodka-based cocktail with muddled blackberries, fresh lime juice, egg white, soda and black rice horchata, which is made in-house from black rice macerated with vanilla bean, woodruff, black cardamom and cinnamon that’s then pureed and sweetened. And don’t forget the grated black cardamom garnish. It’s the little things.
Form of Flattery ($14) at The Commons Club
203 N. Wabash Ave. 312-940-4747
Don’t be fooled by the summery citrus ingredients in this one. The Virgin Hotel bar’s fall spice twist on a Moscow mule features vodka, St. Elizabeth Allspice Dram (a woodsy rum-based liqueur with cloves, cinnamon, nutmeg and pepper), fino sherry, lime juice and calamansi extract (from the mandarin orange-kumquat hybrid fruit), topped with ginger beer. Stop by mid-month when the fall menu is available.
Tom and Jerry ($12) at The Heavy Feather
2357 N. Milwaukee Ave. 773-799-8504
Cold-weather cocktails don’t get much more fun than this classic eggnog variant. Doug Phillips, beverage director at the Slippery Slope’s recently opened upstairs fern bar, mixes brandy, two kinds of rum, cream, egg, cinnamon, clove and vanilla with a sprinkle of nutmeg. Keep an eye out for this one come November.
DARK FRUIT
Fig Fashioned ($9) at Tack Room
1807 S. Allport St. 312-526-3851
Extra dry and black cask rums, housemade fig preserves, house bitters and orange oil—it’s kind of a fig deal at the Pilsen piano saloon tucked inside Thalia Hall.
Frontier Shrub ($12) at White Oak Tavern & Inn
1200 W. Webster Ave. 773-248-0200
If you haven’t met a shrub cocktail yet, let this one be your introduction. New beverage director Michael Pickering uses the colonial technique (macerating overripe fruit in sugar, straining the juice and adding vinegar to balance out the sweetness) with fresh cranberries in this bourbon cocktail with blackcurrant liqueur, herbaceous bitters and a cinnamon garnish. Look for it on the menu in about two weeks.
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CHOCOLATE
Of Quarters & Halves ($12) at The Revel Room
1566 N. Milwaukee Ave.773-278-1600
From the nitro tap of this Wicker Park bar comes this Halfwit Coffee Roasters coffee cocktail with rye whiskey, amaro, chocolate liqueur and coffee bitters. Would you like a little caffeine with that cocktail?
Crafty Kitsune ($13) at Momotaro
820 W. Lake St. 312-733-4818
Who doesn’t love a good combo? This one from the Japanese Fulton Market restaurant is sweet and salty with bourbon, chocolate liqueur, shiro miso syrup and a whole egg served in a coupe with a smoked sea salt rim.
SAVORY
First Fire ($12) at Tete Charcuterie
1114 W. Randolph St. 312-733-1178
It’s butternut squash season, and if you’re like us, you want it in every meal. And now you can have it in a glass with bar director Owen Worley’s smooth, savory scotch concoction with squash juice cooked sous-vide (in an airtight bag that’s placed in a water bath), black cardamom tincture and housemade pecan syrup.
Zuckerman’s Famous Drink ($10) at Longman & Eagle
2657 N. Kedzie Ave. 773-276-7110
Bacon and bourbon go together like bacon and just about everything else. This bacon-fat-washed whiskey cocktail from the Logan Square bar sounds like a great breakfast stand-in with maple syrup, pineapple shrub and lemon juice. And get a kick out of that bacon-jalapeno salted rim.
SMOKY
Maple & Sage ($14) at ETA
455 N. Park Drive 312-840-6600
Leaves and campfire are two autumnal aromas that mean the season is in full swing. Lauren Parton, bar manager at the Loews Hotel’s lobby bar, starts this cocktail off right by smoking the glass with burnt sage before mixing in rum, Spanish white wine and maple syrup with a sage sprig garnish. The pyro in me thinks this drink is fire. Ask for it by name at the bar.
Mr. Dooley ($16) at GreenRiver
259 E. Erie St., 18th floor 312-337-0101
Not sure who Mr. Dooley is, but we like the sound of this cocktail at the new Streeterville Irish-American restaurant, with rye whiskey, herbaceous Amaro Montenegro, a chocolatey syrup made with lapsang souchong black tea and creme de cacao, lemon juice, Orinoco bitters, egg white and a sprinkle of cinnamon.
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