[2] It is believed that the original owners of the land, both Jesse Peebles and Aaron Tilly, were the ones who established the town in 1836.

It is thought that the settlement got its name from the men's hometown of Chesterfield in Derbyshire, England.

By 1949 many educational consolidation issues were solved and Chesterfield students began attending classes at Carlinville High School.

Carlinville, the Macoupin county seat, is 12 miles (19 km) to the east via Routes 111 and 108.

According to the U.S. Census Bureau, Chesterfield has a total area of 0.54 square miles (1.40 km2), all land.