By the 1970's, overcrowding had become a large enough problem at Northeast to warrant the establishment of a second high school in the town.

[2] In February 2008, Chesapeake parents began an organization (CEEDSS) to protest a special education program, known as CRP or the Chesapeake Regional Program, that has been in the school since 1990, but according to parents has been disruptive to education and concealed by administration.

The feeder elementary schools are Lake Shore, Pasadena, Bodkin, and Fort Smallwood.

In addition to including the entire Lake Shore region of Pasadena, Chesapeake's attendance area also covers Gibson Island and the Riverdale neighborhood within Severna Park.

During the 2019–2020 school year, the racial makeup of Chesapeake High School's 1,388 students was 83.6% white, 5.9% Hispanic, 4.1% Black or African American, 1.9% Asian, and 3.9% two or more races.