Chicago Cocktail

Name: Chicago Cocktail with Brandy and Triple Sec
Prep time: 5 min
Total time: 5 min
Yield: 4 servings
Ingredients: 2 oz Mr. Boston Five Star Brandy; 1 dash Bitters; 1/4 tsp Mr. Boston Triple Sec

The Chicago Cocktail is a vintage mixed drink combining brandy, triple sec, and bitters for a balanced, slightly sweet sipper with citrus notes. It's an elegant choice for those who prefer spirit-forward classics.

🏷️Equipment: old-fashioned glass

Total

5 min

Servings

4

Difficulty

Easy

Est. Cost

$10–$16

Recipe Source

View original recipe

From Mr. Boston Drinks · by Mr. Boston Official Bartender's Guide 50th Anniversary Edition

Ingredients

2 oz Mr. Boston Five Star Brandy
1 dash Bitters

1/4 tsp Mr. Boston Triple Sec

3 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 ingredients above with ice and strain into prepared glass.

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Tips & Notes

Pro tips

Chill your glass beforehand by filling it with ice while you prepare the drink; discard ice before serving for a properly chilled cocktail.
Measure precisely: the ratio of brandy to triple sec (8:1) is critical to the drink's balance—use a jigger to avoid over-sweetening.
Use a dash of bitters sparingly; add it last after other ingredients to prevent it from settling at the bottom.
Stir rather than shake if you prefer a silky texture and less dilution; this drink works well either way depending on personal preference.

Substitutions

Mr. Boston Five Star Brandy → VS or VSOP brandy (maintains spirit quality; avoid premium cognac)
Mr. Boston Triple Sec → Orange curaçao or Cointreau (adds depth or premium citrus notes)
Angostura Bitters → Orange or Peychaud's bitters (shifts complexity; stay with one dash)

Storage & make-ahead

Cocktails are best served immediately after mixing and chilling; do not store prepared cocktails.

Equipment

cocktail shaker or mixing glass · jigger · bar spoon · strainer

Common Questions

What type of brandy works best in a Chicago Cocktail?

A five-star or VS (Very Special) brandy like Mr. Boston provides the right balance of smoothness and flavor. Avoid premium cognacs, which are wasted in mixed drinks.

Can I make a Chicago Cocktail without triple sec?

You can substitute orange curaçao for similar sweetness and citrus, but triple sec is traditional. Cointreau will work but will increase cost.

Should a Chicago Cocktail be served cold?

Yes, serve it well-chilled over ice or strain it up (no ice) in a coupe glass after shaking with ice and straining.

What type of bitters should I use?

Angostura bitters is the standard and traditional choice; a single dash is sufficient to add complexity without overpowering the brandy and triple sec.