"Regardless of the spirit or the bitters, the best flavor enhancer for an Old Fashioned is some jazz. And one of our favorite places to go for classic cocktails and live music is Lazy Bird in the West Loop. This dimly lit, 1940s-meets-modernist bar is located in the basement of the Hoxton, and has plenty of soft couches and chairs for you to sink into while listening to some velvety crooning. And though they have an exhaustive cocktail list, everyone knows that the ideal drink to accompany Billie Holiday is a classic Old Fashioned. " - john ringor