Randolph Street Market: Celebrating 20 Years of Style, Community, and Fun

If there’s one thing Chicagoans love about summer, it’s the return of street fests. This year, join us in celebrating the 20th anniversary of one of Chicago’s favorites – the Randolph Street Market! On July 29th and 30th, September 23rd and 24th, and November 11th and 12th, guests are invited to sift through vintage jewelry, art, books, fashion, and decor from over 200 sellers. Set up in a format so that no two booths look the same, guests are sure to spend hours perusing the racks, crates, and shelves worth of items.

Taking place both inside and outside, the parking lot at 1341 W Randolph completely transforms into a European-inspired market full of goodies, food, beverages, and live entertainment. Founder and executive producer, Sally Schwartz, is leaning into the industry-wide shift for small businesses, and continues to give them the perfect place to continue selling to a wide audience in a post-pandemic world. We also got the opportunity to have a conversation with Sally, and hear all about her inspiration, both past and present, as well as where she hopes to take the Randolph Street Market in the future. 


Can you share with us the inspiration behind starting the Randolph Street Market and how you discovered London’s Portobello Road antique flea market?

I love Europe and flea marketing has been a passion of mine since I was little. I collect cigarette lighters and everyone smokes in Europe so when in London in 1996 I went to Portobello Road, which was the fruit and vegetable market, and that’s where the flea market was. Randolph Street/Fulton Market was the historic market district in Chicago so VOILA


How has the Randolph Street Market evolved since its inception, and what are some significant milestones or achievements that you are particularly proud of?

It has changed a lot, started as strictly antiques, nothing 50 years or younger was allowed. Now we love mixing old and new but all “new” must be fair trade overseas, made in the US, and mostly designed and crafted by the people who come onsite and sell.


Vintage and antique markets can be found in various cities around the world. What unique elements and experiences do you believe set the Randolph Street Market apart from other similar markets?

What makes Randolph Street Market so unique are the people because Chicago is like no other place. The melting pot really is a pot of creativity and wonderful educators/sellers, who know the history of their pieces and love to share their vision with the customers.


In your opinion, what role does the Randolph Street Market play in promoting sustainability and preserving cultural heritage through vintage and antique items?

Passing down items is not only keeping history at hand and telling a story about a piece’s origin but it also is not waste in a landfill or creating a carbon footprint.


How do you engage and connect with the local community to foster a sense of belonging and create a vibrant atmosphere at the market?

Everyone is welcome at the Randolph Street Market! The variety, shapes, sizes, sexual orientation, cultural background, color, political preferences, all are welcome and it’s an entirely friendly, open, happy place to be! People are motivated to be onsite, they pay to get in. We have gates surrounding the property and fantastic security. Everyone feels safe and welcome.


What strategies have you implemented to attract both vintage enthusiasts and first-time visitors to the Randolph Street Market, and how do you ensure a memorable experience for all attendees?

I feel the event is a gigantic party, so I am very careful of where and how I place all the vendors so they are having a great time. Making it easy for them to earn money and bringing customers to them via all the various marketing channels brings out the enthusiasts who truly appreciate the offerings of all these dealers. Throw in great food, bars, and eleven live musical acts and the mood is celebratory!


Looking ahead at the next 20 years, what are your future plans and aspirations for the Randolph Street Market? Are there any new initiatives or expansions on the horizon?

I would love to create popups in other cities with the brand name and Chicago vibe! I have plans to have a store, but not sure if I’m cut out for retail! Would love to really do a jumbo NOSTALGIA FESTIVAL in Chicago with all of our legacy brands. Who knows, it could happen!!


The Randolph Street Market takes place at 1341 W Randolph Street this summer on July 29th and 30th, September 234d and 24th, and November 11th and 12th from 10 AM to 5 PM. Buy your tickets HERE!