Savoring the Season: Chicago’s Festive Drink Delights


Get ready for season fun as we explore the best spots in Chicago to enjoy festive drink delights and warm up your winter nights.

Headquarters Beercade

Get ready for festive fun! Reindeer Games Christmas Pop-Up returns to River North’s Headquarters Beercade on November 16th. Decked with holiday decor, the bar will be serving up some deliciously themed cocktails! Expect the Santa’s Slushie (Bourbon Cream and honey over crushed ice), Cutie Pie (Apple Pie Liqueur and hard cider shaken with an apple garnish), and Fireside Old Fashioned (Apple Brandy and orange oil over a big ice cube with toffee garnish)!

Cafe Robey

Nestled within the chic confines of the Robey Hotel in Wicker Park, Cafe Robey beckons with an enticing sip of seasonal allure: the “Fall Romance” cocktail! This exquisite concoction features a harmonious blend of Tequila, cinnamon, hibiscus, and lime. With every sip, you’ll find a new note that reflects the flavors of autumn, naturally making Cafe Robey the perfect destination for those seeking out the essence of fall.

Howl At The Moon 

Why not celebrate with a shot at one of Chicago’s favorite live music and dueling piano bars? From the fruity Strawberry Shortcake to the zesty Cinnamon Toast, there’s a flavor for every palate, and don’t miss out on classics like the Jägerbomb. 

JoJo’s Shakebar 

Discover a world of creamy delights at JoJo’s Shakebar in the heart of River North. As the chill of winter descends upon Chicago, you’ll find solace in their signature Baked Hot Chocolate shake, priced at just $8! This indulgent creation has an abundance of flavors, with a rich fudge brownie baked to perfection and served à la mode. Allow its comforting warmth to reignite your spirit and banish the winter cold!

Vol. 39

Exploring the Chicago-inspired cocktail list at Vol. 39 will leave you wanting them all, so allow us to be your guide. Try the Parcha Colada, a Puerto Rican & German Spirits Encapsulate Humboldt Park in a Pina Colada. Another favorite is the Garfield Park Conservatory Milk Punch, a perfect blend of jungle, desert and forest in Chicago. Another thing we love about this iconic Loop cocktail bar: Every month Vol 39 and a spirits partner donate a combined $2 to a featured charity for every “Classics For A Cause” -cocktail sold. 

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