| Chesapeake to Seymour (Tennessee) | 419.32 mi (674.83 km) |
| Chesapeake to Shady Hills (Florida) | 677.15 mi (1,089.76 km) |
| Chesapeake to Shafter (California) | 2,376.80 mi (3,825.09 km) |
| Chesapeake to Shaker Heights (Ohio) | 434.62 mi (699.45 km) |
| Chesapeake to Shakopee (Minnesota) | 1,055.83 mi (1,699.19 km) |
| Chesapeake to Sharon (Pennsylvania) | 387.14 mi (623.04 km) |
| Chesapeake to Sharonville (Ohio) | 476.45 mi (766.76 km) |
| Chesapeake to Shasta Lake (California) | 2,472.13 mi (3,978.50 km) |
| Chesapeake to Shawnee (Kansas) | 1,020.65 mi (1,642.58 km) |
| Chesapeake to Shawnee (Oklahoma) | 1,156.13 mi (1,860.62 km) |
| Chesapeake to Sheboygan (Wisconsin) | 774.51 mi (1,246.46 km) |
| Chesapeake to Shelby (North Carolina) | 308.34 mi (496.23 km) |
| Chesapeake to Shelbyville (Indiana) | 551.42 mi (887.42 km) |
| Chesapeake to Shelbyville (Kentucky) | 500.76 mi (805.89 km) |
| Chesapeake to Shelbyville (Tennessee) | 572.24 mi (920.93 km) |
