The Chester Yellow Jackets play Illinois high school football (IHSA) as a 2010 member of the Black Diamond conference. Chester High School is located in Chester, Illinois. Chester is in Randolph county. The Yellow Jackets' Illinois Pigskin region is the 618 Football Region. They are coached by Bryan Lee entering his 3rd year of coaching at Chester. The school Athletic Director is Mike Coffey.

The schools 2010 enrollment numbers are 290. The Yellow Jackets' colors are Orange/Black. Chester has qualified for the IHSA playoffs 9 times, the last playoff appearance was 2009. They have qualified for the playoffs 2 consecutive years.