| Chesapeake to Winder (Georgia) | 457.36 mi (736.05 km) |
| Chesapeake to Windsor (California) | 2,521.44 mi (4,057.87 km) |
| Chesapeake to Windsor (Colorado) | 1,560.83 mi (2,511.92 km) |
| Chesapeake to Winfield (Kansas) | 1,138.19 mi (1,831.74 km) |
| Chesapeake to Winnetka (Illinois) | 715.87 mi (1,152.09 km) |
| Chesapeake to Winona (Minnesota) | 953.61 mi (1,534.69 km) |
| Chesapeake to Winston-Salem (North Carolina) | 223.72 mi (360.04 km) |
| Chesapeake to Winter Garden (Florida) | 640.75 mi (1,031.18 km) |
| Chesapeake to Winter Gardens (California) | 2,304.10 mi (3,708.08 km) |
| Chesapeake to Winter Haven (Florida) | 676.32 mi (1,088.43 km) |
| Chesapeake to Winter Park (Florida) | 630.32 mi (1,014.41 km) |
| Chesapeake to Winter Springs (Florida) | 622.76 mi (1,002.24 km) |
| Chesapeake to Winterville (North Carolina) | 100.27 mi (161.37 km) |
| Chesapeake to Winton (California) | 2,421.85 mi (3,897.59 km) |
| Chesapeake to Wisconsin Rapids (Wisconsin) | 886.04 mi (1,425.94 km) |
