Liberty School in Highland Park was built in 1917, as the city population grew rapidly with the rise of the automobile industry. Like all other schools in Highland Park, Liberty had a swimming pool, and every student was expected to learn how to swim. Former mayor of Highland Park Linsey Porter was a student there in the 1950's. On his first day of school the floor was polished so clean that he slipped and fell in the hallway, ending up in the hospital for eight days.
A new wing was added in 1969 to replace portable classrooms that had been erected on the property, as enrollment approached 900 students. However, the neighborhood around Liberty was in transition. A 1971 report noted "The Liberty School attendance area is characterized by an older White population and a younger, low-income Black population . Many of the older families no longer have school-age children which accounts in part for the high percentage of Black students attending the school."
In 1997, Liberty School closed for the first time due to budget problems in the Highland Park School District. It was the latest in a string of closures, including the Community College, Ferris,, Willard, and Field Schools.
The school reopened in September of 2000, renamed the Liberty Academy. 200 students were transferred from a different school, with the goal of bringing enrollment up to 400. Students were expected to perform community service through the Boy and Girl Scout organizations. Initially the school was successful, and by 2001, had 548 students, but the overall population of Highland Park was falling quickly.
Highland Park School District voted to close Liberty Academy on January 20th, 2006. It had just 333 students, operating at half capacity.