Chester High School is an urban, public high school located in Chester, Delaware County, Pennsylvania, United States, with a ZIP code of 19013-4288. Chester is a part of the Chester-Upland School District. The school serves the City of Chester, Chester Township, and Upland. In 2018–2019, the school had 994 pupils.

The first Chester High School building was erected in 1902.

The district offers a wide variety of clubs, activities and sports. Sports programs include; football, basketball, volleyball, cheerleading, baseball, tennis, track and club activities. This school has a long-standing tradition of Championship wins in basketball. The Clippers have won eight state championships: 1983, 1989, 1994, 2000, 2005, 2008, 2011 and 2012. Chester was state runner-up in 1954, 1955, 1957, 1959, 1966, 1967, 1972, 2003, 2007 and 2013. Since the 1981-82 season, Chester has qualified for the state tournament every year except for 1991-92.

• Louis A. Bloom, Pennsylvania State Representative for Delaware County (1947-1952), Judge of the Pennsylvania Court of Common Pleas, Delaware County
• Ethel Hampson Brewster, philologist and professor at Swarthmore College
• E. Wallace Chadwick, U.S. Representative from Pennsylvania
• Tom Chism, professional baseball player
• Walter H. Craig, Pennsylvania State Representative for Delaware County (1923-1925)
• John V. Diggins, former Delaware County Court president judge
• Tyreke Evans, Guard, Memphis Grizzlies
• Negley Farson, author and journalist
• Lenora Fulani, psychologist, psychotherapist and political activist
• Fredia Gibbs, Martial artist, kickboxer, boxer
• Darrin Govens, Guard, St. Joseph University
• Herman Harris, professional basketball player
• Ron Henry, professional baseball player
• Rahlir Hollis-Jefferson, professional basketball player for the Saint John Mill Rats of the NBL
• Rondae Hollis-Jefferson, professional basketball player for the Brooklyn Nets
• Will Hunter, Safety, Minnesota Vikings
• Thaddeus Kirkland, Pennsylvania State Representative and Mayor of Chester
• Wilbur Kirkland, professional basketball player
• Lew Krausse Jr., professional baseball player
• Albert Dutton MacDade, Pennsylvania State Senator and Judge in the Delaware County Court of Common Pleas
• Danny Murtaugh, professional baseball player, coach and manager
• Jameer Nelson, Guard, Orlando Magic and St. Joseph's University
• Curly Ogden, professional baseball player
• Jack Ogden, professional baseball player
• Johnny Podgajny, professional baseball player
• Joe Pyne, controversial talk show host from the 1950s and 1960s
• George Raymond, president of the NAACP Chester branch from 1942 to 1977
• Stefan Roots, Mayor of Chester, Pennsylvania
• Bo Ryan, Men's Basketball Coach, University of Wisconsin–Madison
• Dawn Sowell, professional Track and Field athlete
• William Cameron Sproul, 27th Governor of Pennsylvania
• Ellwood J. Turner, Pennsylvania State Representative for Delaware County (1925-1948), 119th Speaker of the Pennsylvania House of Representatives (1939-1941)
• Horace Walker, former NBA Forward
• William Ward Jr., Pennsylvania State Representative and two term mayor of Chester
• Robert C. Wright, Pennsylvania State Representative

• Chester High School
• Chester High School Marine Corps JROTC

39°51′02″N 75°22′02″W / 39.8506°N 75.3673°W / 39.8506; -75.3673