In 1833, Jesse Morgan, the area's first postmaster, opened the first educational institution for Duneland locals. That school sufficed the community until William Thomas II donated land and offered to help build a two-room schoolhouse in 1840. When the building was finally finished in 1852, there were some local complaints of "its rickety conditions." Twenty-five years later, in 1877, $6,000 was spent on creating Chesterton's first high school. Within only a few years, overcrowding became a problem, and the school received a four-room addition in 1890. This building worked for some time, but complications such as a broken furnace, led to the school building being torn down in 1911. After some property disputes with a local church, it was replaced with a more spacious, two-story school. The community outgrew this school yet again, and in 1921 a school was created specifically for high-schoolers. The school was three stories tall and possessed an auditorium that could seat 750. After spending $175,000, Westchester Township High School opened on December 14, 1922, and was hailed by locals as a wonderful building.
Academic Super Bowl is a local and state competition involving five member teams of students from all grade levels, with members learning detailed information about events and discoveries that occurred over a certain time.
Japan Bowl/Japanese Olympiad
CHS has won the Japan Bowl/Japanese Olympiad state championship nineteen times along with three national Japan Bowl as of 2016.
Chesterton High School offers a number of programs in the visual and performing arts.
Theater
Throughout the academic year, three productions are performed. The first production is in the fall and changes the most from year to year. In the 2011-2012 school year, for instance, the fall play was a dinner theater production catered by local businesses. The winter production is a children's play, with 3rd graders from surrounding elementary schools coming to watch the performances and getting a behind-the-scenes tour. The largest production is the spring musical. Chesterton's 2007 performance of Guys and Dolls was nationally recognized, being called an "extraordinary high school production" by USA Weekend Magazine.
Chesterton High School has two show choirs. The Sandpipers are the most select choral ensemble at Chesterton High School, with both male and female members. The Drifters are the all female show choir competing in the Unisex division. In 2018 both show choirs made it to the FAME National Competition. The Drifters swept the unisex competition, winning the national championship title, and The Sandpipers took second.
WDSO
88.3 is a radio station located at Chesterton High School, with its transmitter located at Chesterton Middle School. WDSO is a non-profit high school station.
