Randolph Street Market, Chicago

Spotlighted by local and national press including TimeOut Chicago, the Wall Street Journal, and Michigan Avenue Magazine, Randolph Street Market's collection of merchants—more than 300 vendors in May–September and 125 vendors in October–April—shows off antique furnishings and vintage wearables from all over the world. Vintage dealers from across the country, including local favorites D. Brett Benson and Man in the Moon, stuff market stalls with men's and women's clothing, estate jewelry, and even vintage fashion magazines. Treasure hunters can investigate indoor booths to fill their closets with items from designers such as Hermes, Pucci, and Dior. In addition to apparel, Randolph Street Market also features hospitality areas brimming with gourmet chocolates, as well as cuisine and drinks from local eateries.