| Pittsfield to Isabela (Puerto Rico) | 1,694.92 mi (2,727.70 km) |
| Pittsfield to Iselin (New Jersey) | 141.06 mi (227.01 km) |
| Pittsfield to Isla Vista (California) | 2,549.49 mi (4,103.01 km) |
| Pittsfield to Issaquah (Washington) | 2,369.57 mi (3,813.45 km) |
| Pittsfield to Ithaca (New York) | 165.31 mi (266.05 km) |
| Pittsfield to Ives Estates (Florida) | 1,204.86 mi (1,939.04 km) |
| Pittsfield to Jackson (Michigan) | 568.81 mi (915.41 km) |
| Pittsfield to Jackson (Mississippi) | 1,161.06 mi (1,868.54 km) |
| Pittsfield to Jackson (Missouri) | 934.75 mi (1,504.33 km) |
| Pittsfield to Jackson (Tennessee) | 956.46 mi (1,539.27 km) |
| Pittsfield to Jackson (Wyoming) | 1,881.99 mi (3,028.78 km) |
| Pittsfield to Jacksonville (Alabama) | 902.50 mi (1,452.44 km) |
| Pittsfield to Jacksonville (Arkansas) | 1,140.99 mi (1,836.25 km) |
| Pittsfield to Jacksonville (Florida) | 958.09 mi (1,541.89 km) |
| Pittsfield to Jacksonville (Illinois) | 901.91 mi (1,451.49 km) |
