I think a classic "South-Side Fizz" from Chicago would be perfectly in line for your Chicago theme.
-2 oz Gin
-3/4 oz lime juice
-1/2 oz simple
-Dash Angostura (optional but I think it adds a touch of complexity)
Shake, serve in a tall glass over ice and top with soda
Alternatively, since taxes are on both candidates agendas, how about an income-tax cocktail?
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try a mitt rumney -
•Peels of 8 lemons
•2.5 cups Demerara sugar
•16 oz Boiling water
•16 oz Fresh lemon juice
•1 (750-mL) bottle Smith & Cross Traditional Jamaica Rum (or other strong, pungent Jamaican rum)
•12 oz VSOP cognac
•12 oz Real peach brandy*
•3 qt (96 oz) Cold water
•Garnish: Grated nutmeg
At least a day ahead, fill a 2-quart bowl with water and freeze until completely solid. In a large punch bowl, muddle the lemon peels and sugar. Let the mixture stand for at least 3 hours. Add the boiling water, stirring until as much as possible of the sugar has dissolved. Add the remaining ingredients and stir to combine. To serve, add the ice block and garnish liberally with freshly grated nutmeg. This recipe serves 25.