| Winter Garden to Isabela (Puerto Rico) | 1,153.22 mi (1,855.92 km) |
| Winter Garden to Iselin (New Jersey) | 927.68 mi (1,492.95 km) |
| Winter Garden to Isla Vista (California) | 2,277.29 mi (3,664.94 km) |
| Winter Garden to Issaquah (Washington) | 2,522.51 mi (4,059.59 km) |
| Winter Garden to Ithaca (New York) | 1,001.85 mi (1,612.32 km) |
| Winter Garden to Ives Estates (Florida) | 198.21 mi (318.99 km) |
| Winter Garden to Jackson (Michigan) | 959.60 mi (1,544.33 km) |
| Winter Garden to Jackson (Mississippi) | 575.44 mi (926.08 km) |
| Winter Garden to Jackson (Missouri) | 767.99 mi (1,235.97 km) |
| Winter Garden to Jackson (Tennessee) | 648.38 mi (1,043.46 km) |
| Winter Garden to Jackson (Wyoming) | 1,914.27 mi (3,080.73 km) |
| Winter Garden to Jacksonville (Alabama) | 439.02 mi (706.53 km) |
| Winter Garden to Jacksonville (Arkansas) | 757.64 mi (1,219.30 km) |
| Winter Garden to Jacksonville (Florida) | 123.77 mi (199.19 km) |
| Winter Garden to Jacksonville (Illinois) | 916.15 mi (1,474.40 km) |
