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Now celebrating its 34th year, Fountain Square Art Festival is the largest and oldest fine arts fair on Chicago's majestic North Shore. Featuring the eclectic works of more than 225 juried artists, this sprawling art showcase epitomizes words like "cosmopolitan” and "sophistication." The festival takes place in downtown Evanston, just steps from the eponymous Fountain Square. It also features a popular children's art tent with fun activities overseen by the acclaimed Evanston Art Center, food, and a soothing jazz-centric music lineup.