| Winter Springs to Isabela (Puerto Rico) | 1,142.60 mi (1,838.83 km) |
| Winter Springs to Iselin (New Jersey) | 910.32 mi (1,465.03 km) |
| Winter Springs to Isla Vista (California) | 2,292.42 mi (3,689.30 km) |
| Winter Springs to Issaquah (Washington) | 2,530.27 mi (4,072.07 km) |
| Winter Springs to Ithaca (New York) | 986.99 mi (1,588.41 km) |
| Winter Springs to Ives Estates (Florida) | 199.80 mi (321.55 km) |
| Winter Springs to Jackson (Michigan) | 952.77 mi (1,533.33 km) |
| Winter Springs to Jackson (Mississippi) | 588.08 mi (946.43 km) |
| Winter Springs to Jackson (Missouri) | 771.43 mi (1,241.49 km) |
| Winter Springs to Jackson (Tennessee) | 653.24 mi (1,051.29 km) |
| Winter Springs to Jackson (Wyoming) | 1,922.83 mi (3,094.50 km) |
| Winter Springs to Jacksonville (Alabama) | 441.81 mi (711.02 km) |
| Winter Springs to Jacksonville (Arkansas) | 767.24 mi (1,234.76 km) |
| Winter Springs to Jacksonville (Florida) | 116.12 mi (186.87 km) |
| Winter Springs to Jacksonville (Illinois) | 917.59 mi (1,476.71 km) |
