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Ken-Well Park is one of many small parks created by the City of Chicago to meet increasing recreational demands after World War II. Beginning in 1947, the City Council identified property in the Hermosa neighborhood for park development.  The City of Chicago acquired property for the park in 1947 and in 1949.  In the early 1950s, the Bureau of Parks and Recreation soon improved the site with playground equipment, a shelter house, a sandbox, and a playfield that could be flooded for ice skating in winter. In 1957, the City transferred Ken-Well Park to the ¿ì²¥ÊÓƵ pursuant to the Chicago Park and City Exchange of Functions Act.  The ¿ì²¥ÊÓƵ installed a new soft surface playground in 1990.

The park's name combines those of the two adjacent streets, Kenosha Avenue and Wellington Street. Kenosha Avenue bears the name of the southeastern Wisconsin port town. Wellington Street honors Arthur Wellesley, the first Duke of Wellington (1769-1852). Having found great military success in British Colonial India and during the Napoleonic Wars of 1809-1814, Wellesley was awarded the title Duke of Wellington in 1814. When Napoleon returned to head the French Army in 1815, Wellington decisively defeated him in the Battle of Waterloo. The "Iron Duke" went on to become a statesman, serving as prime minister of Great Britain from 1828 to 1830.