Chester is located in southwestern Illinois in Randolph County (of which it is the county seat) southeast of St Louis between Red Bud and Murphysboro along Highway 3 overlooking the Mississippi River. The population estimate for July 1, 1998 was 7,639, a decrease of 565 since 1990.

Recreational opportunities include Randolph State Park, Randolph SFWA and Turkey Bluffs SFWA. The town is only minutes from the Fort Kaskaskia River State Park Historical Site (where the Kaskaskia River empties into the Mississippi) to the northwest and the Shawnee National Forest, Kinkaid Lake and Lake Murphysboro State Park to the southeast.

Chester is the birthplace of Elzie Segar, the creator of the cartoon character "Popeye, the Sailor Man". A statue stands next to the Chester Bridge as a tribute. In addition, the annual "Popeye Picnic" is held the weekend following Labor Day.