Norfolk County had been losing territory for nearly a century. As Norfolk, Portsmouth, and other cities annexed land from the surrounding county, the county shrank. By the 1950s the small city of South Norfolk - which had become an independent city in 1922 to escape annexation by Norfolk - was facing the same problem. Independent cities in Virginia could not annex from each other, but they could from counties. South Norfolk feared losing all the county land adjoining it; Norfolk County feared losing what was left. The merger let both jurisdictions stabilize their borders forever. The wave of consolidations in southeastern Virginia between 1952 and 1975 reshaped the political map of the region; Chesapeake's 1963 creation is the largest of those reshapings.

The Dismal Swamp Canal runs through Chesapeake. George Washington was one of the surveyors who laid it out in the 1760s - he was an investor in the Dismal Swamp Company and walked the swamp himself - and a section of the route is still informally called Washington's Ditch. The canal begins at the Deep Creek section of the city, where it branches off from the Southern Branch of the Elizabeth River, runs alongside U.S. 17 into North Carolina, and connects to Elizabeth City. It is the oldest continuously operating man-made canal in the United States, in service for more than 220 years. The canal locks at Great Bridge mark the transition between the Southern Branch and the Chesapeake and Albemarle Canal - and the locks sit at the site of the December 9, 1775 Battle of Great Bridge, where Patriots ended Lord Dunmore's military presence in Virginia.

Much of southwestern Chesapeake is occupied by the Great Dismal Swamp National Wildlife Refuge - one of the largest remaining intact swamps on the East Coast. The refuge stretches across the Virginia-North Carolina border, harboring Lake Drummond at its heart, and supports black bears, bobcats, more than 200 bird species, and a centuries-old human history. Maroon communities of escaped enslaved people lived in the depths of the swamp from the late 1600s into the Civil War, hidden by water and cypress. Today the refuge is one of the largest protected wetlands in the Mid-Atlantic. The city manages the conflict between development and conservation that this geography forces - Chesapeake is one of the largest cities in the United States by area, and most of that area is still farmland, forest, or swamp.

Chesapeake's water supply is a challenge the city's geography keeps making harder. The Northwest River in the southeast of the city supplies most of the drinking water, but the river is brackish - the salt content fluctuates with the tides and the weather - so in the late 1990s the city installed an advanced reverse-osmosis treatment system at the Northwest River plant. Groundwater is no longer reliably available across most of the area. To supplement, Chesapeake and Virginia Beach together draw additional fresh water from Lake Gaston, eighty miles to the west on the Virginia-North Carolina border, through a 76-mile, 60-inch pipeline that follows the former right-of-way of the abandoned Virginian Railway. The system can pump sixty million gallons a day. Living in a city built between two swamps and a sound costs more than most people realize.

Some of what Chesapeake carries is hard to talk about lightly. In 2003 the city hosted the first trial of Lee Boyd Malvo, then seventeen, one of the two D.C. snipers - a change-of-venue case from northern Virginia. He was convicted of murder and sentenced to life without parole. On November 22, 2022, six Walmart employees - Randy Blevins, Fernando Chavez-Barron, Tyneka Johnson, Lorenzo Gamble, Brian Pendleton, and Kellie Pyle - were killed by their night-shift supervisor at a Walmart Supercenter off Battlefield Boulevard, three days before Thanksgiving. Most days, Chesapeake is the kind of city it set out to be in 1963: stable, growing, residential, second-largest in the state, with NASCAR drivers Ricky Rudd and Brenden Queen, NBA Hall of Famer Alonzo Mourning, the saxophonist Clarence Clemons, and pop singer Ava Max on its roll of natives. The hard days do not erase the ordinary ones. They sit next to them.