Sally Schwartz never set out to run a vintage empire, but after more than two decades of transforming parking lots into treasure hunts, the Randolph Street Market has become a Chicago institution.
The beloved bazaar kicked off its 22nd season this weekend in the West Loop with more than 200 dealers, live music and a variety of food vendors.
“It’s the dealers that make this market so special and the fact that they’re all great people,” said Schwartz, who founded the event in 2003 after years of party planning and flea market hunting. “They’re collectors themselves. Some are the first ones at estate sales, others fly across the country to find perfect pieces and they all bring in the most amazing, curated merchandise.”
This year’s market offered an eclectic blend of vintage fashion, art, records, salvaged furniture, ephemera and global artifacts. Shoppers browsed rows of vendor tents while enjoying live music, cocktails and local bites.
The market also featured swing dance lessons and other whimsical touches like a Victorian-style photo booth and a clown-poet named Mosey Posey, who played ukulele around the grounds, Schwartz said.
“I look at this whole thing like a floor plan,” Schwartz said. “It’s my party-planner brain. I’m thinking about the energy in each corner. Who’s next to whom, where can we add a pop of color or a burst of sound? I want people to spend the whole day here, not just shop and leave.”
Photographer Jose Fernandes, who was selling prints framed in reclaimed New Orleans wood by his wife, said the market’s eclectic energy felt like home.
“We love vintage,” he said. “There’s a real crossover between what we create and the uniqueness of this market.”
For Schwartz, cultivating that crossover has been deliberate, and sometimes challenging.
“When I rebranded from the Chicago Antique Market to Randolph Street Market in the mid-2000s, some of the older dealers panicked and thought I was turning into a flea market,” Schwartz said. “But I believed we could keep the antiques and bring in something new, which was artists, up-cycled goods and handmade items. Now that mix is what makes this thrive.”
The market’s diversity is another point of pride, Schwartz said. The vendors represent a mix of ethnicity, sexual orientations and age groups, she said.
“I hope this creates an environment where everyone feels welcome,” Schwartz said. “Anyone can come here alone and feel like they belong.”
Mohamed Tourey, a longtime vendor from Gambia, echoed that sentiment. His booth displayed moon masks, beaded crowns and colorful glass jewelry imported from Africa.
“This show supports us,” Tourey said. “It’s big and people show up, so I come back every year.”
So does Wendy Marrero of Windy City Wendys, who refurbishes furniture and resells vintage collectibles.
“That connection among vendors and between us and the customers is what makes this special,” Marrero said.
Schwartz said the market has changed significantly since she first opened it on the streets of the West Loop.
“There was no social media back then, so I used to print flyers and run full-page ads in the Tribune,” Schwartz said. “Now the younger dealers are teaching the older ones how to use social media and helping us bring in new customers.”
Even with its growth, Schwartz said her goal remains the same: to create a joyful, safe and welcoming environment.
“I want everyone who walks through the gate to feel happy,” Schwartz said.
The Randolph Street Market returns Sept. 27-28. In the meantime, Schwartz will host the Vintage Shindig and record fair in Highland Park.
“I’d love to just come here and be invisible one day so I could wander around like any other shopper and take it all in,” Schwartz said, smiling. “That’s the dream.”
