Chicago’s best wine destinations, according to the experts

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On his nights off, you might expect to find Derrick Westbrook, the Chicago wine director and sommelier, formerly of the Michelin-starred Elizabeth in Lincoln Square, unwinding in similarly gilded hot spots. After years of working restaurant floors, Westbrook admits he enjoys fine dining from the unique lens of a guest. But when Westbrook is off the clock, he’s not known to frequent spots boasting deep collections of classified Bordeaux or upscale steakhouses specializing in cult Napa cabs. “Honestly, you’re most likely to find me having wine or beer at the Bronzeville Winery,” Westbrook says. “I’m a little biased because I...