In 1946, residents living on the western edge of Omaha sought a way to maintain quality education in their rural schools. The Boards of Education of Districts 19, 31, 46 and 65 met to decide whether combining resources would better address individual differences in children. After careful study, a committee of experts proposed a merger of the four districts into one. This group suggested that the districts use existing school facilities for students in grades K through 6. The committee also suggested that a new high school be designed and built with the specific developmental and academic needs of students in mind.

A series of joint meetings during the winter culminated in the merger of districts 31, 46 and 65 to form District 66 in March 1947 (District 19 chose not to join). The first three schools in the new District were Oakdale, Underwood Hills and Loveland.

The junior-senior high school opened its doors in 1952. The school was built on farmland near 87th and Pacific Street. The current high school still sits on that site today. The new name reflected the three former districts on what was then the western edge of Omaha when District 66 became known as the Westside Community Schools.

Thanks to the generosity and support of District 66 voters in 2015, Westside Community Schools was able to invest in the construction and renovation of several schools throughout the district. Oakdale, Sunset Hills, and Swanson were all open to students by the 2019-2020 school year; Westside Middle School and Westside High School were improved and expanded; security upgrades and facility improvements were made throughout the district; and Prairie Lane Elementary is expected to open to students in 2021.