Old Town Art Fair 2027

The Old Town Art Fair takes place June 12-13, 2027, on the streets of the historic Old Town Triangle neighborhood on Chicago's near north side. Considered one of the top outdoor fine art shows in the nation and celebrated for over 75 years, the fair is managed entirely by volunteers. Fair proceeds support nonprofit organizations including the Menomonee Boys and Girls Club, local schools, community groups, and neighborhood improvements.

The fair features a maximum of 235 booths and attracts discerning, art-educated art buyers in a direct-to-consumer sales model. A single booth costs $800 (including a $25 Itinerant Merchant Fee required by the City of Chicago); a limited number of double booths are available at $1,800. Artists are juried into one of several media categories: 2-D Mixed Media, 3-D Mixed Media, Ceramics, Digital Art, Drawing/Pastel, Fiber, Glass, Jewelry, Metal, Painting, and Photography. An Emerging Artist category is available for artists ages 18-25, recently graduated (within 2 years), or who have made a recent career change to the Visual Arts, with a reduced application fee of $20.

Cash awards are given for First and Second Place in each media category, plus an additional Best of Show award. Artists retain all proceeds from sales. Benefits include a website gallery with artist information and link, organized load-in and cooperative load-out, complimentary continental breakfast on both days, booth sitters, complimentary water and snacks, express food concession lanes, reserved artist parking, and access to indoor bathrooms and water filling stations. Application deadline is January 15, 2027. Jurying occurs January 22-24, 2027, with jury invitations sent February 8, 2027. Booth fee is due March 1, 2027. On-site check-in and setup is June 11, 2027. The fair runs 10 AM-7 PM on June 12 and 10 AM-6 PM on June 13, rain or shine.