Vintage Events in Chicago

Check out happening vintage events all around Chicago, IL

Cupid's Vintage & Artisan Fest presented by Windy City Market

 Sat, 07 Feb at 12:00 pm Artifact Events USD 0 to 9

Pickwick Vintage Show in Chicago | April 2026

 Sun, 19 Apr at 10:00 am Chicago Athletic Association - The Unbound Collection by Hyatt USD 12

The 25th anniversary…. Midwest Awards Ball presents POP CULTURE ICONS: I ❤️ The 90s!

Sat, 25 Apr at 05:00 pm The Grand Ballroom Chicago

Vintage House Market w/ Tigermilk

 Sun, 18 Jan at 12:00 pm Emporium Arcade Bar

Winter Fashion Ball 2026 — A Charitable Museum Gala

 Sat, 24 Jan at 05:00 pm 4722 W Armitage Ave USD 90 to 295

Pilsen Vintage Market

 Sun, 22 Feb at 12:00 pm 2317 W 18th St Free