Highland Park's first high school opened in 1887 on top of a paint store at the corner of Second Street and Central Avenue and was originally named Deerfield Township High School. Two teachers taught 60 students in the school comprised of three rooms. The first year's courses included arithmetic, civil government, rhetoric, zoology, English literature and a voluntary Latin class. Of the $3,000 budgeted for that year, only $2,772.39 was spent.
In 1890, a Board of Education was elected for what was ultimately to become Township High School District 113.
Due to a growing population, the high school moved to a larger location on the corner of St. John's and Vine Avenue in 1900 and was renamed Deerfield Shields High School, after James H. Shields who was a community leader in educational affairs. In 1904, Lake Forest High School merged with Deerfield Shields, which increased District 113's tax support. Over the next 30 years, five buildings were added to the high school's original structure and enrollment increased by more than 1,000 students.
In 1936, Lake Forest built its own high school and Deerfield Shields High School was renamed Highland Park High School, which it remains today.
About a year later, a delegation of men from the Village of Deerfield confronted the Board of Education about constructing another high school in their community. However, members decided to build one high school instead that could house 2,000 students.
In 1954, HPHS was completely modernized and expanded. A music and industrial arts building was erected as well as a cafeteria and gym/pool complex.
Almost immediately after the additions were completed, the board began planning for an oncoming population explosion. In 1956, voters approved the site purchase for a second high school to be located in Deerfield. Two years later, a more than $4 million bond issue was passed by residents to build another school, which was to be named Deerfield High School.
In 2000, HPHS and DHS underwent a two year, $75 million renovation and expansion project.
Highland Park High School currently has more than 2000 students enrolled and around 300 staff members. The facility houses about 45 clubs and nearly 30 sports teams. Highland Park High School is accredited by the state of Illinois and the North Central Association and is a member of NACAC, IACAC, and the National college Board; and adheres to the NACAC Statement of Principles and Good Practice.