Wilson Park was created by the Old Portage Park District, one of 22 independent park commissions consolidated into the Chicago Park District in 1934. Established in 1912, the Old Portage District spent years developing its first property, Portage Park. By the mid-1920s, the surrounding Portage Park community had grown considerably, and its far northeastern corner was in need of its own recreational facilities. Residents suggested developing an 8.81-acre property along Milwaukee Avenue, but the Street Railway Company planned to build a car barn there instead. Frank J. Wilson, a former Cook County Commissioner and committeeman for the old 41st Ward, led a successful fight to secure the property as parkland. The park district recognized Wilson's efforts by naming the new park in his honor.

The Old Portage Park District began improving Wilson Park with walkways, lawns, and planted areas in 1925. Three years later, a Georgian Revival-style fieldhouse was built along Milwaukee Avenue. The handsome brick building, with its limestone accents and columned portico, is identical to fieldhouses at nearby Shabbona and Chopin Parks. The Wilson Park fieldhouse was soon surrounded by a playground, a putting green, horseshoe and tennis courts, and a sunken lawn for baseball, football, and skating in winter.

Soon after acquiring Wilson Park in 1934, the Chicago Park District laid new concrete sidewalks, rehabilitated the landscape, and remodelled the fieldhouse. The building accommodated a wide variety of community activities including lectures, movies, theater productions, club meetings, ping pong, tumbling, wrestling, and social dancing. Significant recent improvements to Wilson Park include a soft surface playground, a sand volleyball court, and an interactive waterplay area.