Overview The Old Town Art Fair is a juried fine art fair run by volunteers through the tree-lined streets of Chicago's Old Town Triangle Historic District, and the same weekend more than 60 gardens open to visitors, many of them private and seen only during the fair. More than 200 artists from across the United States and Canada show each year, picked by an independent jury, and nearly half are new to the fair every time. Only original work made by the artist is allowed: no reproductions, no crafts, and the artist has to be in the booth. It falls on the second weekend of June. The Old Town Triangle Association, a neighborhood nonprofit, has run it since the 1950s, and 2026 was the 76th fair. On site Five gates ring the district, with the main gate at Lincoln Avenue and Wisconsin and the fair centered on the Triangle Center on North Park Avenue. Booths line the residential blocks, and the Garden Walk is a self-guided route through the neighborhood's private gardens, with maps at every gate and in the fair's app telling the history of the houses and the people who lived in them. Two stages play jazz, swing, folk and blues: the Plaza Stage at Wisconsin and Orleans and the Food Court Stage at North Park and St. Paul, where Old Town restaurants sell lobster rolls, tacos, pork belly and pizza with beer and wine. The Children's Corner at Wisconsin and Sedgwick runs magic shows, children's theater and craft tables staffed by neighborhood schools. In 2026 a Community Corner added local nonprofit art groups and emerging artists. Audience People come to buy. The fair says exhibiting artists often call it their most successful event of the year, and it describes its crowd as enthusiastic collectors. The Wells Street Art Festival runs a few blocks south the same weekend, so organizers steer visitors to the Brown Line at Sedgwick and the Clark, Broadway, North Avenue and Armitage buses rather than scarce street parking. Families come too, and the fair gently asks people to leave their dogs at home for the sake of the glass and ceramics. Talent and Influencers Awards go out by medium every year. In 2026 Dennis Angel took Best of Show for drawing and pastel, Eric Doctors won ceramics, McKenzie Grimmer 2D mixed media and Nicario Jimenez 3D mixed media. Each fair has its own poster artist, and the fair keeps an archive of its posters going back to the 1950s. Track record ArtFairCalendar.com has voted it the top art fair in America in multiple years. More than 600 neighbors and friends run it, and proceeds have let the Old Town Triangle Association give more than $2.5 million to neighborhood nonprofits, including the Menomonee Club, local schools, children's programs and historic preservation projects. Brand presence Sponsorships are tax-deductible gifts to the association. The top sponsor is named first on all promotional material and on every fair poster, hangs a banner at all five entrances, takes a free booth on the grounds and is named on the booths of the poster artist, the nonprofit artist and the emerging artist, in the printed and mobile guides and in geo-fenced ads over fair weekend. Lower levels share entrance signage and guide listings and each get a booth. The live music stage carries its own sponsor, and sponsors are also listed at the fair's spring benefit at the Chicago History Museum.