| Chesapeake to Shelton (Connecticut) | 362.05 mi (582.66 km) |
| Chesapeake to Shelton (Washington) | 2,472.47 mi (3,979.06 km) |
| Chesapeake to Shenandoah (Louisiana) | 949.63 mi (1,528.29 km) |
| Chesapeake to Shepherdsville (Kentucky) | 523.91 mi (843.15 km) |
| Chesapeake to Sheridan (Wyoming) | 1,688.49 mi (2,717.36 km) |
| Chesapeake to Sherman (Texas) | 1,164.79 mi (1,874.55 km) |
| Chesapeake to Sherrelwood (Colorado) | 1,565.45 mi (2,519.35 km) |
| Chesapeake to Sherwood (Arkansas) | 899.28 mi (1,447.25 km) |
| Chesapeake to Sherwood (Oregon) | 2,462.92 mi (3,963.68 km) |
| Chesapeake to Shiloh (Illinois) | 755.54 mi (1,215.92 km) |
| Chesapeake to Shiloh (Ohio) | 481.56 mi (774.99 km) |
| Chesapeake to Shiloh (Pennsylvania) | 229.23 mi (368.91 km) |
| Chesapeake to Shirley (New York) | 339.04 mi (545.63 km) |
| Chesapeake to Shively (Kentucky) | 532.00 mi (856.17 km) |
| Chesapeake to Shoreline (Washington) | 2,436.79 mi (3,921.64 km) |
