| Chesapeake to Olympia Heights (Florida) | 793.31 mi (1,276.70 km) |
| Chesapeake to Omaha (Nebraska) | 1,104.44 mi (1,777.42 km) |
| Chesapeake to On Top of the World Designated Place (Florida) | 627.56 mi (1,009.95 km) |
| Chesapeake to Onalaska (Wisconsin) | 928.11 mi (1,493.64 km) |
| Chesapeake to Oneida (New York) | 443.43 mi (713.63 km) |
| Chesapeake to Oneonta (New York) | 404.55 mi (651.06 km) |
| Chesapeake to Ontario (California) | 2,316.66 mi (3,728.30 km) |
| Chesapeake to Ontario (Oregon) | 2,177.62 mi (3,504.53 km) |
| Chesapeake to Opa-locka (Florida) | 780.19 mi (1,255.59 km) |
| Chesapeake to Opelika (Alabama) | 585.22 mi (941.83 km) |
| Chesapeake to Opelousas (Louisiana) | 1,000.93 mi (1,610.84 km) |
| Chesapeake to Orange (California) | 2,333.18 mi (3,754.89 km) |
| Chesapeake to Orange (Texas) | 1,101.96 mi (1,773.44 km) |
| Chesapeake to Orange City (Florida) | 608.07 mi (978.59 km) |
| Chesapeake to Orangeburg (South Carolina) | 339.09 mi (545.71 km) |
