Old Town Art Fair 2026

The Old Town Art Fair will take place on June 13-14, 2026, on the streets of the historic Old Town Triangle neighborhood on Chicago's near north side. Celebrated for more than 75 years, this is considered one of the top outdoor fine art shows in the nation. The fair features 235 maximum booths with single booths (10' deep x 15' wide) at $800 and a limited number of double booths (10' deep x 30' wide) at $1,500. Artists must submit 5 images of artwork only and be present during all festival hours.

The fair offers cash awards for First Place and Second Place within each of the four media groupings, with an additional Best of Show award. Artists retain all proceeds from the sale of their art and receive various benefits including website gallery listing, organized load-in and load-out, complimentary continental breakfast, booth sitters, reserved artist parking, and express lanes at food concessions. Media categories include 2-D Mixed Media, 3-D Mixed Media, Ceramics, Digital Art, Drawing/Pastel, Emerging Artist, Fiber, Glass, Jewelry, Metal, Painting, and Photography.

The application deadline is January 15, 2026, with jurying on January 23-24, 2026, and invitations sent February 1, 2026. Booth fee payment is due by March 1, 2026, with no refunds after this date. The fair is produced by the Old Town Triangle Association, a nonprofit neighborhood organization, with proceeds supporting local community groups and organizations.