Hop off at the Violet Hour for the frothy, gin-based Thumb in the Pie cocktail ($12) (1520 N Damen Ave, 773-252-1500. El: Damen).
Venture below ground for the potent Merry Mai Tai ($11) in the converted bank vault at the Bedford (1612 W Division St, 773-235-8800. El: Division).
Kick things off with a refreshing sake cocktail, such as the Cucumber Sakerita ($9), at the bar at Mana Food Bar (1742 W Division St, 773-342-1742. El: Division).
Last stop: The Charleston, where Annemarie Katz features fancy Jell-O shot cocktails ($3–$4) on Wednesday nights (2076 N Hoyne Ave, 773-489-4757. El: Western).