Overview Randolph Street Market is an antiques and vintage market in Chicago's West Loop that fills Plumbers Hall, terrazzo floors and all, and the lot beside it with about 200 dealers, and Travel and Leisure, Architectural Digest and USA Today have each named it one of the top 10 flea markets in the country. The stalls run to antiques, vintage fashion, fine art, vinyl, estate jewelry, home decor, global goods and handmade work from indie designers. In November and December it turns into the Randolph Street Holiday Market, indoors only. Sally Schwartz's Chicago event company, Image Pilots, started the market in 2003; she founded the company in 1985 as Paint Me A Party Productions. On site A festival weekend runs 10 a.m. to 5 p.m. both days, rain or shine: the September 2026 festival was set for 125 dealers inside the hall and 75 in tents on the asphalt outside, with live music, DJs, food vendors and three market bars pouring Bloody Marys, margaritas, mimosas and spirit tastings. A children's area inside the hall hands out treasure maps. Dogs are welcome outdoors but not in the building. Two ATMs sit on site because many dealers prefer cash, and a delivery service takes furniture home. The Holiday Market puts 125 dealers indoors with a DJ, a market bar and a Little Elves Workshop, and opens each Saturday with an early-buy hour whose proceeds go to the Dr. Martin Luther King Jr. Boys and Girls Club. Audience Shoppers pay to get in, and the market describes them as upscale and motivated. They come to buy, often big: the on-site delivery service exists for furniture, and cash buys room to negotiate. The September 2026 festival was billed around the kind of pieces interior designers and fashion stylists hunt for. Brand presence Companies outside the market's own vendor categories come in as sponsors rather than dealers, on pricing set by market month, with discounts for sponsors who sign on for several months. Past sponsors on the market's own list include Nordstrom, Alfa Romeo, Johnnie Walker and The New York Times.