| Winona to Oskaloosa (Iowa) | 196.87 mi (316.83 km) |
| Winona to Oswego (Illinois) | 234.92 mi (378.07 km) |
| Winona to Oswego (New York) | 757.08 mi (1,218.41 km) |
| Winona to Otsego (Minnesota) | 127.48 mi (205.16 km) |
| Winona to Ottawa (Illinois) | 235.55 mi (379.09 km) |
| Winona to Ottawa (Kansas) | 420.18 mi (676.21 km) |
| Winona to Ottumwa (Iowa) | 212.87 mi (342.59 km) |
| Winona to Overland (Missouri) | 375.99 mi (605.10 km) |
| Winona to Overland Park (Kansas) | 389.42 mi (626.71 km) |
| Winona to Overlea (Maryland) | 844.32 mi (1,358.79 km) |
| Winona to Oviedo (Florida) | 1,210.58 mi (1,948.24 km) |
| Winona to Owasso (Oklahoma) | 579.43 mi (932.50 km) |
| Winona to Owatonna (Minnesota) | 77.63 mi (124.93 km) |
| Winona to Owensboro (Kentucky) | 495.32 mi (797.14 km) |
| Winona to Owings Mills (Maryland) | 829.84 mi (1,335.49 km) |
