| Winston-Salem to Isabela (Puerto Rico) | 1,459.48 mi (2,348.80 km) |
| Winston-Salem to Iselin (New Jersey) | 445.90 mi (717.61 km) |
| Winston-Salem to Isla Vista (California) | 2,221.81 mi (3,575.66 km) |
| Winston-Salem to Issaquah (Washington) | 2,260.15 mi (3,637.36 km) |
| Winston-Salem to Ithaca (New York) | 481.91 mi (775.56 km) |
| Winston-Salem to Ives Estates (Florida) | 700.60 mi (1,127.51 km) |
| Winston-Salem to Jackson (Michigan) | 478.62 mi (770.27 km) |
| Winston-Salem to Jackson (Mississippi) | 625.51 mi (1,006.66 km) |
| Winston-Salem to Jackson (Missouri) | 527.16 mi (848.38 km) |
| Winston-Salem to Jackson (Tennessee) | 480.87 mi (773.89 km) |
| Winston-Salem to Jackson (Wyoming) | 1,687.28 mi (2,715.42 km) |
| Winston-Salem to Jacksonville (Alabama) | 349.06 mi (561.76 km) |
| Winston-Salem to Jacksonville (Arkansas) | 672.61 mi (1,082.46 km) |
| Winston-Salem to Jacksonville (Florida) | 406.99 mi (654.99 km) |
| Winston-Salem to Jacksonville (Illinois) | 597.99 mi (962.38 km) |
