| Winona to Orangeburg (South Carolina) | 931.37 mi (1,498.90 km) |
| Winona to Orangevale (California) | 1,567.39 mi (2,522.47 km) |
| Winona to Orchards (Washington) | 1,506.08 mi (2,423.81 km) |
| Winona to Orcutt (California) | 1,649.15 mi (2,654.05 km) |
| Winona to Oregon (Ohio) | 448.64 mi (722.02 km) |
| Winona to Oregon (Wisconsin) | 138.19 mi (222.39 km) |
| Winona to Oregon City (Oregon) | 1,512.09 mi (2,433.48 km) |
| Winona to Orem (Utah) | 1,055.04 mi (1,697.93 km) |
| Winona to Orinda (California) | 1,637.55 mi (2,635.38 km) |
| Winona to Orland Park (Illinois) | 256.26 mi (412.41 km) |
| Winona to Orlando (Florida) | 1,217.94 mi (1,960.09 km) |
| Winona to Ormond Beach (Florida) | 1,173.20 mi (1,888.08 km) |
| Winona to Oro Valley (Arizona) | 1,314.87 mi (2,116.08 km) |
| Winona to Oroville (California) | 1,563.11 mi (2,515.59 km) |
| Winona to Oshkosh (Wisconsin) | 154.31 mi (248.33 km) |
