Randolph Street Market Festival – May Market

The Randolph Street Market Festival returns May 24–25 for its 2025 season opener, transforming Chicago’s West Loop into a vintage treasure hunt and entertainment extravaganza. Recognized as one of the top antique and vintage markets in the country, this indoor/outdoor festival features 200+ dealers from across the U.S., offering a curated mix of antiques, art, indie designer goods, jewelry, vinyl, and global finds. Shoppers will enjoy live music all weekend long, including rockabilly, blues, Latin salsa, country western, and Sunday morning jazz brunch performances, plus poetry readings and DJ sets. Foodies can savor local fare from top vendors, sip seasonal cocktails from three full-service bars, and enjoy new attractions like Sunday Swing Dance Lessons. With activities for all ages, it’s the ultimate Chicago weekend.