The Port of Chesapeake is located on the Elizabeth River in Virginia's coastal plain, or Tidewater, region. Part of the Chesapeake Bay Waterway, the Port of Chesapeake is almost nine nautical miles (11 kilometers or 7 miles) south-southeast of the Port of Portsmouth. The Port of Chesapeake is about 20 kilometers (13 miles) south-southeast of the Port of Norfolk. The 2010 US Census reported a population of over 222 thousand in the Port of Chesapeake.

The Port of Chesapeake became an independent city in 1963 when South Norfolk and Norfolk County were merged. The Port of Chesapeake is the largest city in Virginia by area (914 square kilometers or 353 square miles), and the Port of Chesapeake contains both farmlands and parts of the Great Dismal Swamp. The Port of Chesapeake is crisscrossed by inland waterways. The Port of Chesapeake is a major oil storage center and has several port facilities. Manufactured products produced in the Port of Chesapeake include cement, steel products, fertilizer, and lumber. Other important economic sectors include greenhouses, nurseries, and truck farms.

The Chesapeake (or Chesepian) people were a tribe in the Powhatan confederacy. They lived in the area containing what would become the Port of Chesapeake. Their main village, Skicoak, was in what is now Sewell's Point in downtown Norfolk, Virginia, where a Native American burial mound was found. The Chesapeake also had two villages in today's Virginia Beach where archaeologists have discovered many artifacts and some remains of the indigenous people. It is believed that the Chesapeake people belonged to the Carolina Algonquian group.

Historians believe the Powhatan all but eliminated the Chesapeake people before European settlers arrived in the future Port of Chesapeake area. In 1607, there were about 100 Chesapeake warriors, suggesting a total population of about 350. By 1669, the Chesapeake had disappeared as distinct tribe. In 1775, the Battle of Great Bridge took place near the site of what would become the Port of Chesapeake.

The Port of Chesapeake was part of the Virginia Colony and Norfolk County from 1691. The Port of Chesapeake was created during the era of local government change in southeastern Virginia that took place between 1952 and 1975.

Before the latter decades of the 20th Century, the Port of Chesapeake was a bedroom community for Norfolk and Virginia Beach. In the 1980s and 1990s, the Port of Chesapeake began to grow as industries began to grow in the area. Rapid growth created significant strains on the Port of Chesapeake's municipal infrastructure ranging from congested schools and roads to saltwater in the city's water supply.

In 2003, the Port of Chesapeake got national attention when a change of venue moved the first trial of 17-year-old Beltway sniper Lee Boyd Malvo to the city. The Port of Chesapeake jury spared Malvo the death penalty and sentenced him to life without parole. Neighboring Virginia Beach's jury sentenced his partner, John Allen Muhammad, to death.

The Port of Chesapeake city is made up of farmland, forests, wetlands, and a few urban areas. The Port of Chesapeake has miles of industrial, commercial, and residential properties on the waterfront. Today, the Port of Chesapeake is the third most populous city in the Commonwealth of Virginia. In 2008, Money Magazine recognized the Port of Chesapeake as the 85th of the "Best Places to Live." In 2011, Bloomberg Businessweek named the Port of Chesapeake the 21st best city in America.

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