Joseph Sears envisioned a community of congenial child-focused families in a beautiful country setting near the convenience of the city. Sears, who had pleasant memories of an 1883 family trip to Kenilworth, England, chose the same name for the new village. After purchasing the land between Wilmette and Winnetka in 1889, he laid pipes for water and gas, paved the streets, and planted trees before lots were designated and houses built. Lot prices were higher than those of the villages nearby, with restrictions concerning lot sizes, high quality construction, homogeneous structures, and inhabitants. The village qualified for incorporation in 1896 with a population of 300.

Kenilworth attracted the attention of many visitors to the Chicago Columbian Exposition of 1893, including famous architects and landscape planners. Franklin Burnham, who had the same Swedenborgian roots as Joseph Sears, designed the founder’s home. Additionally, Burnham played a significant role in the aesthetic of the Village by designed the railroad station and several other homes. Jens Jensen provided landscape planning for many parks and homes. George W. Maher, a contemporary of Frank Lloyd Wright, designed the fountain, accompanying benches, town posts, and many homes, which reflected the strong influence of the Arts and Crafts and Prairie styles.