Randolph Street Market

In honor of the fall season, Chicago’s signature open-air market, the Randolph Street Market, is hosting its fall market with vintage treasures, live bands, food and fun on September 27–28, 2025, in the West Loop.

Photo courtesy of Randolph Street Market

Celebrating 22 years, the Randolph Street Market Festival features an intriguing mix of vintage and antique finds like apparel, housewares, jewelry, vinyl records and art as well as contemporary goods.

Photo courtesy of Randolph Market

The market helps celebrate the season with 125 vendors and mini-boutiques offering a curated mix of one-of-a-kind finds. The event also supplies cocktails, DJs, kids’ crafts and informal modeling showcases.

Browse through the unusual lineup of dealers that showcase goods that span all the way from the 1890s through the 2000s. Score unforgettable pieces that reflect specific eras and historical periods.

Photo courtesy of Randolph Market

Sample different dishes at the food stalls to munch on breakfast goodies, sweet treats or full-fledged meals. Sip on beer, wine, Bloody Marys, Margaritas, Mimosas, and assorted spirit samplings.

Food vendors scheduled for these dates include Happy Lobster, Rainbow Thailand, All Belgium Waffles, Maggie’s Sweets and Tasting India. Don’t miss the exciting line-up of non-stop live bands.

Randolph Street Market is the ultimate shopping mecca but it also supplies festival appeal with live music, food, and cocktails. The market runs from 10 am-5 pm, outdoors and indoors, rain or shine. Tickets are $12 in advance and $15 at the door. Students, seniors and military admission is only $5.. Children under 12 can enter for free. Arrive early for ample street parking or opt for valet.