Until Winston's Cafe came along, staying up all night in the Uptown
neighborhoods usually meant you were up to no good. That may or may not still be the case, but either way, this coffee house is open and serving hot joe 24/7. Whether you're winding down from a night out at the nearby bars and restaurants, or just getting your day started, Winston's is there for you.
The open, airy space has been converted from one of the area's most notorious leather bars into this stylish beanery by former Chicago Eagle manager and bartender Jim Stephens. Formerly, the few always-open options in the area were limited to greasy spoons and not much else. Stephens hopes to create a draw simply by being there, and in this neighborhood renowned for its active nightlife, young professionals, and artistic bent, a fashionable cafe that never shutters fits in just perfectly.
The large, expansive windows brighten the exposed brick walled space during the day, contrasting with the dimly lit nighttime hours of the shop. Both times suit the cafe quite well, though, and the attractive, espresso colored tables for two are inviting whether bathed in sunlight or spotlighted by one of the chic lamps hanging overhead.
Winston's offers coffee and tea from Metropolis. Locally crafted sandwiches are available for less than $5, and the wifi is free.
Average cost: <$10
Centerstage Reviewer: Bill Burman