Randolph Street Market Festival – September 27–28

Start: Saturday, September 27, 2025 10:00AM
End: Sunday, September 28, 2025 5:00PM

America’s Largest Urban Antiques Market Returns to the West Loop for Its Final Indoor-Outdoor Event of the Season, Featuring Vintage Finds, Local Eats, Craft Cocktails, and Live Entertainment. Since 2003, Randolph Street Market has been recognized as one of the country’s top urban antique and vintage festivals. More than 200 dealers from across the nation will showcase a curated mix of art, antiques, indie fashion, vinyl, estate jewelry, and global goods, offering something for collectors and casual shoppers alike. “We’ve always believed in creating a space where people can discover something unexpected, connect with local creatives, and just have fun,” says Sally Schwartz, founder of Randolph Street Market. “It’s more than a market—it’s a celebration of style, community, and Chicago’s incredible spirit.” Featured Vendors • Wini and I – Vintage designer fashion & jewelry • Barrovian Books – Handbound journals • Dollsauce Vintage – Bold 80’s casuals & knick-knacks • Windy City Racks – Newspaper box storage • Off The Wall Art • Dick Russell’s Estate Sales – 26-foot semi of antiques from Cleveland • Black Cat Curiosities • Industrial Cottage • Vintage Barware • Coup de Lux • Thrifty Fashionista Food & Drink Highlights • Happy Lobster • J Spice • Roost Chicken & Biscuits • Mr. Greek • Avrom Farms Fajitas • Hey Beignet! • All Belgium Waffles • Oberweis Ice Cream • Maggie’s Sweets • Dar Baklava • Sunflower Coffee Café • Windy City Shaved Ice • Tredici Macarons Specialty Vendors Include: CRAFIAN Artisanal Toffee, Chef Heatley’s Hot Sauce, Sweet Crunch Tangali, The BG Bakery, Dinky Delights, Schweet Cheesecake & Chili, XOXO Chicago Dubai Chocolate, Citrus Sisters, Uni Uni Bubble Tea, and a Tea Workshop. Live Entertainment Schedule Saturday: • Poems-While-You-Wait (vintage typewriters) • DJ Sets: Dave House, Crate Digga Hash, DJ Tigs Outside Band Stage: • 10:00–11:30 AM: Woodstreet Bloodhounds – Bluegrass & Country Swing • 11:30 AM–1:30 PM: Feel Good – 1980s & Classic Dance Covers • 1:30–3:00 PM: Maxwell Street Blues Band with Lowreen – Chicago Blues • 3:00–5:00 PM: Contrabanda Latin Jazz Band – Salsa Rhythms Sunday: • Typewriter Tarts • DJ Sets: Dave House, Crate Digga Hash, BTiggs Outside Band Stage: • 10:00 AM–12:00 PM: Tony Morrison Jazz Quintet with Robin Watson – Swing Brunch • 12:00–2:00 PM: Joe Wortell & His Country Band • 2:00–3:30 PM: Michelle Billingsly – Bold Vintage Vocals • 3:30–5:00 PM: Al Simon & the Saturn Kings – Rockabilly Revival About Randolph Street Market Now in its 22nd year, the Randolph Street Market Festival is home to the world-renowned Chicago Antique Market, Indie Designer Market, Modern Vintage Chicago and the Holiday Market. Touted as a “mecca of cool,” “the best hotspot for antiquing” and “the Barneys of vintage” by Travel & Leisure, The New York Times, Lucky, Architectural Digest, USA Today, Elle Décor, goop, and more, it’s Chicago’s most exciting shopping destination. The market supports local charities including Project Onward, PAWS, Chicago House, Chicago’s Children’s Charities, Chicago Lights Tutoring, I Grow Chicago, and others. Tickets: • General Admission: $12 online / $15 at the gate (valid both days) • Early Buying Saturday: $25 (access at 9 AM; benefits Boys & Girls Club) • Seniors (65+), Students, Military, First Responders: $5 with valid ID • Children under 12: Free