Toast the Season with Holiday-Inspired Cocktails Around Chicago

Gather with friends and family to cheers the holiday season with fun themed cocktails at bars and restaurants around the city.

The city of Chicago is getting into the holiday spirit by stringing lights, hanging garland, and displaying other Christmas decor. Many of Chicago's popular establishments are serving up holiday fare, including specialty cocktails, to ignite the Christmas cheer in all of us. No matter where you live, work or hang out, enjoy some of our favorite holiday libations. 

If fancy is your name but saving money is your game, head to DECA inside the Ritz Carlton for their DECAdent holiday happy hour daily from 4:30pm to 7:30pm. Sunday through Thursday they will feature one of their specialty seasonal mixes for just $10.

Deca Lounge + Bar, 160 E. Pearson, 312-573-5160

  • #SundayFunday - Spiked Cider with caramel, apple cider, and prosecco
  • #MondayBlues - Spiked Hot Cocoa with peppermint schnapps, hot chocolate, and a cognac marshmallow
  • #TipsyTuesday - Winter Wonderland Daiquiri with winter infused rum, champagne, and lemon juice
  • #WhiskeyWednesday - Old Man Jed with cinnamon infused local whiskey and house made apple cider
  • #ThirstyThursday - Grin and Pear It with pear vodka, caramel simple syrup, and pomegranate juice

If you love Christmas movies, check out CH Distillery's take on A Christmas Story. Through December 23, you can experience Christmas: A Cocktail Story at the West Loop Distillery where you'll be welcomed by decorations inspired by the 1983 film. Browse through the Bigbee Company Holiday Catalogue and Menu to pick from several whimsical cocktails served in unique vessels. Most cocktails are $13.

CH Distillery, 564 W. Randolph, 312-707-8780

  • Pumpkin Pie Hot Buttered Rum with CH Rum, CH Bourbon, Spiced Butter, Cool Whip, and Nutmeg
  • Dar Glog served in a souvenir mug while supplies last with Red Wine Mulled with Spices and CH-City Winery Rosso Vermouth
  • Uncle Eddie's Frozen Egg Nog with CH Rum, CH Bourbon, House Batter, and Spices 
  • Chile Chocolate Phosphate with CH Dogma Amargo de Chile, Cocoa Syrup, Acid Phosphate, Soda, and Whipped Cream
  • Bowling Ball with CH Bourbon, CH City Winery Rosso Vermouth, CH Fernet Dogma, Coffe Reduction, Orange Bitters
  • Solid Soap Shot with CH Rum, Lavender CH Key Gin, Blueberry, Lemon, Cinnamon, Gelatin, and Coconut "Soap" Foam
  • Fortune Cookie (serves 2) with Green Tea-Infused CH Rum, Apple Cider Cinnamon Orgeat, Grapefruit, and Lime Bitters
  • BB Gun with Cranberry-Infused CH Bourbon, CH Amaro, Maple, Lemon, and Egg White
  • Gingerbread Mule - CH Vodka, Gingerbread Spices, Fresh Ginger, Brown Sugar, Citrus Snowball
  • Eight Magical Nights with CH Aquavit, Gentiane, Lingonberry, and Lemon
  • Mistletoe Gin and Tonic with CH London Dry Gin, Winter Tonic, Lime Cordial, and Rosemary

Keeping with themes, Old Town's Rabbit Hole, which opened in September, invites everyone to experience the magic of wonderland year round. The Alice in Wonderland-themed bar and restaurant has everyone going mad, especially during the holidays with their recently launched winter cocktail menu. All specialty cocktails are $12.

The Rabbit Hole, 1208 N. Wells, 312-274-1824

  • Candy Cane with Tito's Vodka, Godiva White Chocolate, Rumplemintz, and a Candy Cane Garnish
  • Have We Gone Mad with Vanilla Vodka, Earl Gray Tea, and House-Made Lavender Syrup Garnished with Lemon
  • Cranberry Spiced Old Fashioned with Breckenridge Bourbon, House-Made Cranberry Spiced Syrup, Angostura and Orange Bitters Garnished with an Orange Swath and a Fresh Cranberry
  • Winter Solstice Sangria with Lavis Pinot Grigio, Combier, White Grape Juice, Prosecco, and Rosemary Garnish

If spiked classics are your jam, check out Fremont in River North. Their cocktail game is strong and overflowing with fun! They're serving up a Boozy Hot Chocolate and an Irish Coffee Selection both $12. Fremont lets guests be part of the crafting experience and is known for their garnish game!

Fremont, 15 W. Illinois St, 312-874-7270

  • Boozy Hot Chocolate featuring a base of Starbucks cocoa powder, steamed milk and vanilla with your choice of one liquor or liqueur add-in (standouts include Woodford Reserve, Rumpleminze, Absolut Vanilla, Fireball, Bailey's Irish Cream), and two holiday flare toppings (i.e. marshmallows, peppermint sticks, chocolate straws, whipped cream, and sprinkles)
  • Irish Coffee with Corsica Blend by La Colombe and your choice of one liquor and two toppings.

If you're more daring, love taking risks, and live to try something new, head over to SPiN for a creative spin on basic hot chocolate for just $9. SPiN's Food and Beverage Director, Ed Porter, known for his appearance on Food Network's show Guy's Grocery Games, is the brains behind this innovative cocktail.

SPiN, 344 N. State, 773-635-9999

  • Cabernet Hot Chocolate with Lindt Excellence 90% Cocoa Dark ChoclaChocolatem, Milk, and Cabernet Garnished with Spiced Whipped Cream

And finally, if you prefer something a bit more exotic with some ethnic flair, Federales has a delicious spiked horchata with a caffeine kick on the menu for $12. Celebrate the season with this comforting cocktail that stays true to Federales' fiesta vibe.

Federales, 180 N. Morgan, 773-831-9696

  • Boozy Espresso Horchata with Rumchata, an Avion Espresso Floater, and Cinnamon Dusting