The Chester Bridge was constructed in 1942 at a cost of $1.4 million. The bridge allowed vehicles to cross the Mississippi River between Perryville, Missouri, and Chester, Illinois without using a ferry. The Chester Bridge was re-constructed in 1944 after a severe storm destroyed the main span. 

Until 1989, the Chester Bridge was a toll bridge. 

This truss bridge has 14 spans for a total length of 2,827 feet. There are 2 main spans of 670 feet each. The bridge accommodates two lanes of traffic and is 22 feet wide with a vertical clearance of 19 feet 6 inches (permitted). Today, the bridge carries  7,000 vehicles daily, with approximately 25% being commercial motor vehicle traffic.