| Chesapeake to Iselin (New Jersey) | 289.45 mi (465.82 km) |
| Chesapeake to Isla Vista (California) | 2,432.78 mi (3,915.18 km) |
| Chesapeake to Issaquah (Washington) | 2,422.78 mi (3,899.09 km) |
| Chesapeake to Ithaca (New York) | 398.56 mi (641.43 km) |
| Chesapeake to Ives Estates (Florida) | 774.72 mi (1,246.79 km) |
| Chesapeake to Jackson (Michigan) | 577.98 mi (930.17 km) |
| Chesapeake to Jackson (Mississippi) | 846.48 mi (1,362.28 km) |
| Chesapeake to Jackson (Missouri) | 737.35 mi (1,186.65 km) |
| Chesapeake to Jackson (Tennessee) | 702.16 mi (1,130.01 km) |
| Chesapeake to Jackson (Wyoming) | 1,867.55 mi (3,005.53 km) |
| Chesapeake to Jacksonville (Alabama) | 568.70 mi (915.24 km) |
| Chesapeake to Jacksonville (Arkansas) | 894.82 mi (1,440.07 km) |
| Chesapeake to Jacksonville (Florida) | 536.46 mi (863.35 km) |
| Chesapeake to Jacksonville (Illinois) | 784.20 mi (1,262.04 km) |
| Chesapeake to Jacksonville (North Carolina) | 147.93 mi (238.07 km) |
