The first public schoolhouse in Chester was erected in 1858. It was known as the "Pride of Southern Illinois" and is spoken of as "an ornament to the place and a lasting monument to the intelligent spirit of the citizens of Chester."
School records are incomplete until 1873 when the first Board of Education was organized on August 19, 1873. Members of the board included: C.B. Cole, Charles Wassell, Christian Wagner, William Roberts, Jacob Gnaegy and John Baumann.
In 1882, as a result of 24 year of development, the "Pride of Southern Illinois" became a spacious handsome structure of brick. At this time board members who were influential in working on the project were Dr. Wm. A. Gordon, F. Bueckman, and Dr. W.R. McKenzie, Mr. R.W. Mathews was superintendent from 1878-1882 and George L. Guy from 1882-1885. Eight teachers were employed the year 1882-1883, and they were paid salaries amounting to $3700 dollars. Three years later, in 1885, the first class graduated from Chester High School. Members of this class were Eloise Harmer, Dane Williams, Eunice Anderson, Sara Tate, Martha Nesbitt, Eliza Mann, Mary Alice Crisler and Susannah Tate.
In 1904, the Chester Public School changed again when a third wing was added to the building. No class was graduated that year, so it is believed that a fourth year's work was added to the curriculum. J.M. Dickson was the superintendent from 1893-1905.
The progress of our educational system continued when a movement was started in 1924 to build a separate building for the high school. This was completed in 1926 and the first class graduated in 1927. Mr. Elroy W. Hoeb was superintendent. Ten years later under the superintendency of Mr. W.R. Lowry, a gymnasium was added.
The "Wheel of Progress" continued to turn for Chester. In 1949, the voters of School District No. 77 approved bonds to build a new elementary school. The need for improving the educational facilities for public school elementary purposes was quite evident due to the inadequacies of building facilities and outmoded equipment.
During the period of construction, the Chester Public School District No. 77 began to expand as adjacent rural districts requested a partnership with the city system. On August 4, 1953, Community Unit District No. 139 was formed as a result of a positive approval by the electorate. This vote incorporated an area approximately 100.1 square miles in size, into a school district of which the people in this area may well be proud. On February 7, 1954, the new "Chester Community Grade School" was dedicated and a new era of public education was born in the Chester School District.
On October 10, 1955, a committee from the Chester Parent Teacher Association met with the Board of Education to review the overall building plan which had been submitted by the superintendent in regard to an addition to the Chester High School and to the new Community Grade School.
On February 20, 1958 the architectural firm of Bartels and Associates was requested to work with the superintendent and submit prints of building needs of the Chester School District. On the fourteenth day of May 1960, the voters of Chester Community Unit No. 139 approved a proposition to bond the district for $800,000 for the purpose of building additions to the Chester High School and Chester Community Grade School.
Since the bonding power of the district was limited to $600,000 at the time of the issue, the Board of Education approved the high school addition as the first project from the voted bonds.
The highlight of the addition at the grade school included a large gymnasium with folding seating for 570 fans located at the end of the new addition. Dressing rooms and shower facilities are available for physical education and athletics. The gym was built on a lower level so that entrance to it must be made at the ground level into a lobby overlooking the floor.
The completed high school building included the most modern laboratories for "quality" education of the 60's new science laboratories for physics, chemistry, biology, home economics, shop, drafting and electronics comprise one area of the new building. Building arrangement makes it possible for students enrolled in advanced chemistry, physics and biology to do high school research. The music room is large enough for band and chorus plus practice rooms and offices. The new spacious gymnasium is large enough for 2000 fans and dressing areas are provided for both physical education and athletics, coaches and officials to have separate facilities for dressing area, showers, etc. The lobby of the gymnasium is a combined cafeteria large enough to seat 150 students. This cafeteria is adjacent to the new kitchen.
On July 13, 1961, the Board of Education passed a resolution to dedicate the new gymnasium in memory of Daniel N. Colbert, past president of the Board of Education and who had served 16 years as a member of the Board. The resolution called for lettering to be installed on the building as follows: "Colbert Memorial Gymnasium." This is an appropriate dedication since Mr. Colbert, better known as "Dan" to all, contributed 16 years of his time and energies to the building of a better educational system for the children of the Chester School District. Dan died November 5, 1960, while still active as a member of the Community Unit Board of Education.
A severe storm in the summer of 1980 ripped the roof off of Colbert Gymnasium. But the building underwent major renovation including a new gym floor.
The school underwent major renovations to both wings of the school. No more early dismissals because of heat and humidity, with the exceptions of Marie Juergens Gym and Daniel Colbert Gym, the school is air-conditioned.
In 2001, Chester High School opened up a new wing which was constructed on the west side of Colbert Gym. Four classrooms and a weight room were added to the school.