Chicago mixologists share their best holiday cocktail recipes

Billy Sunday Rosy Cheeks Recipe

Holiday party season in full swing, so we tapped three of the city’s top behind-the-bar talents to divulge their go-to seasonal cocktail recipes.

The result: Two super-festive punches and an indulgent, whimsical martini—all begging to be served at your next gathering.  

Billy Sunday Rosy Cheeks Drink

Stephanie Andrews, bar director at the nationally acclaimed Logan Square cocktail bar Billy Sunday, shared a recipe she says captures the holiday spirit and tastes “balanced yet boozy.”

The best thing about serving punch? It’s prepared ahead of time, allowing you to spend your evening mixing and mingling instead of shaking and stirring.

Rosy Cheeks

20 ounces cranberry syrup (recipe below)
1 1/2 cup gin
3/4 cup Cocchi Americano
1/3 cup Gran Classico Bitter
3/4 cup lemon juice
1 bottle sparkling wine
Orange slices, star anise, and cranberries for garnish

Cranberry Syrup

4 cinnamon sticks
2 star anise pods
4 cups frozen or fresh cranberries
1 orange, peeled and juiced
1 vanilla bean, split
2 cups dry white wine
2 cups water
2 cups sugar

Make cranberry syrup: toast cinnamon sticks and start anise pods in a large pan over medium heat. Add cranberries, orange, split vanilla bean, and white wine. Bring to a simmer, then add water and bring to a boil. Boil until cranberries burst, then reduce heat and steep for 30 minutes. Pour mixture through a fine strainer. Stir in sugar.

Pour syrup and remaining ingredients into a punch bowl containing a large ice block. Top with sparkling wine. Garnish with orange slices, star anise, and cranberries.

Serves 8-10.

Lost Lake Cardinal Punch

If you’ve ever been to his Avondale tiki temple Lost Lake, you know Paul McGee is the master of rum-based concoctions.

“Making this punch has become my tradition during the holiday season,” McGee says. “It’s a crowd-pleaser but is also complex with the flavors of ripe red fruit, vanilla, and baking spices.”

Cardinal Punch

3 cups Smith and Cross Overproof Jamaican Rum
2 cups Syrah
1 cup Cocchi Di Torino Sweet Vermouth
2 cups fresh lime juice
2 cups simple syrup (1 part sugar to 1 part water)
2 cups brut sparkling wine
½ ounce St. Elizabeth Allspice Dram
Peel of 1 orange
Orange wheels studded with cloves for garnish

Combine all ingredients aside from the sparkling wine and refrigerate overnight. Remove orange peel and pour mixture into a punch bowl. Add sparkling wine and garnish with studded orange wheels.

Serves 8-10.

Worms in Dirt Drink

They say the holidays bring out the child in all of us, and bar manager Tim Hollingsworth of The Robey Chicago’s rooftop lounge Up & Upcrafted a dessert-like drink that harkens back to your candy-crazed youth.

“We worked with the team at Dylan’s Candy Bar to transform a nostalgic treat into adults-only form,” he says.

Worms in Dirt

1½ ounces milk
1 ounce Irish cream (see recipe below)
1 ounce Hangar 1 vodka
½ ounce Cynar liqueur
½ ounce St. George NOLA coffee liqueur
1 teaspoon crème de cacao
1 teaspoon crème de menthe
Simple syrup, crushed Oreo cookies, and gummy worms for garnish

Irish cream (makes about 1 quart)

1¼ cups Tullamore Dew
1 tablespoon ground espresso
1 14-ounce can sweetened condensed milk
½ cup heavy cream
1 tablespoon cocoa powder
1 tablespoon vanilla extract

Rim a coupe glass with simple syrup and dip into crushed Oreos. Combine all ingredients in a cocktail shaker and shake vigorously. Add ice and shake again. Pour into prepared glass and garnish with gummy worms.

Yields one cocktail.