Chicago Cocktail

Name: Chicago Cocktail with Brandy and Bitters
Prep time: 5 min
Total time: 5 min
Yield: 4 servings
Ingredients: 2 oz Old Mr. Boston Five Star Brandy; 1 dash Bitters; 1/4 tsp Old Mr. Boston Triple Sec; 1 slice Lemon [For the Glass]; Powdered Sugar [For the Glass]

The Chicago Cocktail is a straightforward brandy-based drink combining Old Mr. Boston Five Star Brandy with a dash of bitters and a hint of triple sec, served with a signature sugared lemon rim.

🏷️Equipment: old-fashioned glass

Total

5 min

Servings

4

Difficulty

Easy

Est. Cost

$13–$21

Recipe Source

View original recipe

From Mr. Boston Drinks · by Mr. Boston Deluxe Official Bartender's Guide

Ingredients

2 oz Old Mr. Boston Five Star Brandy
1 dash Bitters

1/4 tsp Old Mr. Boston Triple Sec

1 slice Lemon [For the Glass]

Powdered Sugar [For the Glass]

5 Ingredients

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Instructions

1
Prepare old-fashioned glass by rubbing slice of lemon around rim and then dip in powdered sugar.
2
Stir above ingredients with ice and strain into prepared glass.

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Tips & Notes

Pro tips

Chill your glass before pouring to maintain the cocktail's temperature and crispness.
Use fresh lemon for the rim garnish—the oils enhance the aroma and complement the brandy's complexity.
Measure the triple sec precisely with a measuring spoon; it's a small but crucial amount that balances the brandy's strength.
Stir or shake with ice briefly before straining to properly chill and dilute the spirit.

Substitutions

Old Mr. Boston Five Star Brandy → cognac or VSOP brandy (higher quality, richer flavor)
Powdered sugar → superfine sugar (slightly less texture, similar sweetness on rim)

Storage & make-ahead

Cocktails are best consumed immediately after preparation; store any leftover brandy in a sealed bottle at room temperature.

Equipment

bar jigger · cocktail glass · bar spoon

Common Questions

What type of brandy should I use for a Chicago Cocktail?

Old Mr. Boston Five Star Brandy is the traditional choice, though any quality brandy with similar proof and character works well.

How do I prepare the sugared lemon rim?

Rub the rim of the glass with a lemon slice, then dip it into powdered sugar to coat evenly before pouring the drink.

Can I make this cocktail without triple sec?

Triple sec is a small but important component for balance; omitting it changes the flavor profile significantly, though you can reduce the amount if preferred.