Windy City Espresso Old Fashioned
A bold espresso-infused Old Fashioned combining coffee richness with classic whiskey warmth, perfect for an evening in Chicago. This cocktails & drinks ready in about 7 minutes brings together bourbon, fresh espresso, demerara syrup for a refreshing, crowd-pleasing drink — a bright, easy pour for parties, gatherings, or any warm-weather afternoon when you want something festive without alcohol-only options. Each serving lands at about 220 calories and feeds 1, so it works for entertaining, brunch, or a non-alcoholic option at the bar cart. Tap "Plan a meal with the AI" below to drop this recipe into your week and send the ingredients straight to Instacart. Nutrition values are approximate, calculated from USDA FoodData Central (fdc.nal.usda.gov) — verify against ingredient labels for any health-driven dietary plan.
Ingredients
- 2 oz bourbon
- 1 oz fresh espresso
- 1/4 oz demerara syrup
- 2 dashes chocolate bitters
- 1 wide strip orange peel
- 1 large ice cube
Instructions
- Step 1: Place a large ice cube into a rocks glass and set aside.
- Step 2: Fill a mixing glass with ice cubes. Pour 2 oz bourbon, 1 oz freshly brewed espresso (cooled), and 1/4 oz demerara syrup.
- Step 3: Add 2 dashes of chocolate bitters and stir gently with a bar spoon for 30 seconds until well chilled.
- Step 4: Strain the mixture over the large ice cube in the rocks glass.
- Step 5: Express the oils of a wide strip of orange peel over the surface by holding it skin side down and twisting, then rub the peel around the rim and rest it on the glass edge.
Equipment for this recipe
Top-rated tools to make this recipe successfully.
Frequently asked questions
How long does Windy City Espresso Old Fashioned take to make?
Total time is about 7 minutes (7 min prep + 0 min cook). Most home bartenders find this fits a single afternoon; scale up the batch for parties or pitchers.
How do I store leftover Windy City Espresso Old Fashioned?
Refrigerate any leftover windy city espresso old fashioned in a sealed pitcher or jar for up to 3–4 days. Do not reheat — drinks are served chilled. If the recipe uses sparkling water or fresh herbs, hold those back and add fresh just before pouring so the drink stays bright and fizzy.
Can I substitute ingredients in Windy City Espresso Old Fashioned?
Yes — most ingredients in this recipe have flexible swaps. For oil, use any neutral high-smoke-point oil (avocado, grapeseed, refined coconut). For aromatics, dried herbs at ⅓ the volume of fresh work in a pinch. The full ingredient list is shoppable on Instacart so you can see substitutes in real time.
How do I scale Windy City Espresso Old Fashioned for a different number of people?
The recipe is written for 1 servings. Multiply each ingredient by (your serving target / 1). Cook time stays roughly the same up to 2x; for 3-4x batches, switch from a skillet to a sheet pan or stockpot so the food isn't crowded — overcrowding steams instead of browns.
What goes well with Windy City Espresso Old Fashioned?
Cocktails & Drinks cocktails & drinks like this pair well with a simple grain (rice, couscous, or crusty bread), a quick salad with acid (lemon vinaigrette, pickled onions), and a pan sauce or yogurt-based dip. Tap "Plan a meal with the AI" to get specific side suggestions.
