Guide to the Perfect Night on Randolph Street

By Sarah Freeman

It’s 4:45 PM, and closing time is close enough to taste the fresh air waiting outside those office doors (or are they prison doors?). The sounds of cocktail shakers and sizzling meats taunt as the remaining seconds wind down. Then it’s time for freedom - cue the mass exodus to the bars and restaurants. Tonight’s target: Randolph Street.

Unfortunately, a few hundred other post-work imbibers had the same idea and made a beeline straight for the hottest street in Chicago. How quickly a night’s high expectations can be thwarted with long lines, crowded bars and no reservations. Have no fear; all is not lost. Click through the below slideshow for a foolproof guide to the perfect night on Randolph Street.