| Chesapeake to Oswego (Illinois) | 730.53 mi (1,175.68 km) |
| Chesapeake to Oswego (New York) | 468.14 mi (753.40 km) |
| Chesapeake to Otsego (Minnesota) | 1,077.32 mi (1,733.78 km) |
| Chesapeake to Ottawa (Illinois) | 744.98 mi (1,198.94 km) |
| Chesapeake to Ottawa (Kansas) | 1,044.00 mi (1,680.16 km) |
| Chesapeake to Ottumwa (Iowa) | 915.99 mi (1,474.15 km) |
| Chesapeake to Overland (Missouri) | 780.85 mi (1,256.66 km) |
| Chesapeake to Overland Park (Kansas) | 1,013.70 mi (1,631.39 km) |
| Chesapeake to Overlea (Maryland) | 185.98 mi (299.31 km) |
| Chesapeake to Oviedo (Florida) | 622.46 mi (1,001.76 km) |
| Chesapeake to Owasso (Oklahoma) | 1,083.35 mi (1,743.49 km) |
| Chesapeake to Owatonna (Minnesota) | 1,024.80 mi (1,649.26 km) |
| Chesapeake to Owensboro (Kentucky) | 599.37 mi (964.59 km) |
| Chesapeake to Owings Mills (Maryland) | 190.74 mi (306.97 km) |
| Chesapeake to Owosso (Michigan) | 603.65 mi (971.47 km) |
