If treasure hunting had a social calendar, Randolph Street Market Festival would be the belle of the ball - and in 2026, she’s booked, busy and ready to sparkle!
Exciting event schedule for Randolph Street Market 2026.
Mark your calendars (in bold, preferably with a vintage fountain pen), because the 2026 season kicks off Memorial Day weekend with the beloved Garden Party Market, May 23–24. Think of it as Chicago’s most fashionable rite of spring, where over 200 vendors transform the West Loop into a Parisian-style flea market bursting with antiques, art, fashion, and fabulous finds.
From there, the market keeps the party going all year long:
- July 25–26, 2026 – Summer market magic with breezy fashion and sun-soaked treasures
- September 26–27, 2026 – Fall fashion + home décor takeover (hello, cozy chic!)
- November 14–15, 2026 – Holiday Market kickoff, perfect for early gift hunters
- December 12–13, 2026 – Final festive fling with all the sparkle and stocking stuffers
All events run from 10 a.m. to 5 p.m. and take place in the West Loop at 1341 W. Randolph Street, with holiday markets tucked indoors nearby, ideal for those brisk Chicago days.
Calling this a “flea market” is like calling champagne “sparkling wine.” Yes, you’ll find vintage treasures, but you’ll also discover curated booths that look like designer showrooms, racks of one-of-a-kind fashion and décor pieces that whisper, “Take me home, darling.”
Add in live music, DJs, global food vendors and even cocktail bars, and suddenly you’re not just shopping - you’re experiencing.
Because no two visits are ever the same. One weekend you might score a mid-century bar cart worthy of a Mad Men reboot, and the next you’re leaving with vintage Chanel, a Turkish rug and a newfound obsession with estate jewelry. (It happens.)
It’s also a favorite among designers, stylists and collectors who treat the market like their personal playground - proving that great style isn’t bought off a rack, it’s discovered.
In a city that knows how to do summer (and shopping), Randolph Street Market remains a must-do ritual - part treasure hunt, part street festival, and all-around fabulous.
So, grab your most comfortable chic shoes, channel your inner vintage vixen and prepare to dig for diamonds in the West Loop. Because at Randolph, the thrill isn’t just in the find, it’s in the hunt (AND the party surrounding it!) (All details here!)
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