6 Best Places for Fall Cocktails in Chicago

Fall is in the air…And your glass should be too!

If you’re looking to change up your rosé and sangria routine from the summer, look no further. Here are some of the best fall cocktails around the city to enjoy on those crisp autumn nights.



Joy District

fall cocktails chicago
Photo Credit: Joy District

112 West Hubbard Street


Head to Joy District before the temperature drops again, for cocktails on the roof. For $14, they serve Sliced Pear Moscow Mules, Allspice Manhattans, and Apple Cider Mimosas. Don’t miss Hot Whiskey Maple Cider too, garnished with a mini apple cider donut from Beaver’s Donuts.



The Whistler

fall cocktails chicago
Photo Credit: The Whistler

2421 North Milwaukee Avenue

The Whistler is always changing up their cocktail menu. Their fall line-up has hit the bar just in time for you to enjoy them at Whistler Jam, their weekly event featuring live jazz music at 9pm on Monday nights. Fall cocktails include:


Toleen: Rum, Thai Red Beans, Coconut, Almond Milk, Vanilla, Ramazzotti, Angostura, Spice

Herbs in Horto “City in a Garden”: London Dry Gin, Amer, Cranberry, Lime, Besk, Salt, Gold Style


Jerk Old Fashioned: Bonded Bourbon, Jamaican Rum, Allspice, Falernum, Honey-Salt, Sichuan Peppercorn




fall cocktails chicago
Photo Credit: The Promontory

5311 South Lake Park Avenue West

Mama D’s Pumpkin Pie is back! Hyde Park residents will tell you this is a must-try for fall. When pumpkin spice lattes aren’t cutting it anymore, this cocktail made with brown butter control pisco, pumpkin soda, graham cracker syrup, and maple whip is a major step up!




fall cocktails chicago
Photo Credit: Raised

1 West Upper Wacker Drive

When the temperature drops you’ll still be able to enjoy riverfront views. The Trial By Fire, containing Ketel One Citron, Frangelico, cream, orgeat, egg, black walnut bitters, and torched sugar, will help keep you warm! This is just one of the nine Autumn Originals featured on their cocktail menu.



fall cocktails chicago
Photo Credit: aliveOne

2683 North Halsted Street

You only need to go a few blocks east of Diversey station to get a Brown Line (drink) with Jameson, yellow chartruese, lemon, and orange bitters, or a Cooler by the Lake vodka cocktail at aliveOne.



fall cocktails chicago
Photo Credit: Remedy

1910 North Milwaukee Avenue

Remedy has no shortage of fall drinks. Stop in during their pumpkin carving parties on October 16 and 18 to try them out. The cocktail menu features:

The White Walker: cold brew coffee, Jameson, Bailey’s, Fernet, and house made mint syrup

Apple Crisp: apple cider, lemon juice, simple syrup

Sailor Jerry: spiced rum and prosecco

That’s My Jam: Letherbee gin, creme de cassis, jammy sweet vermouth, lemon juice, black walnut bitter

No Stout About It: Left Hand milk stout, Meyers dark rum, Aztec chocolate bitters, Angostura bitters, simple syrup, a sprinkle of nutmeg


Cheers to Fall!

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