| Chicago to Imola | 4,678.38 mi (7,529.13 km) |
| Chicago to Impruneta | 4,688.14 mi (7,544.83 km) |
| Chicago to Induno Olona | 4,503.92 mi (7,248.35 km) |
| Chicago to Inverigo | 4,523.64 mi (7,280.09 km) |
| Chicago to Inveruno | 4,517.92 mi (7,270.89 km) |
| Chicago to Inzago | 4,542.16 mi (7,309.90 km) |
| Chicago to Iseo | 4,559.40 mi (7,337.64 km) |
| Chicago to Isernia | 4,896.50 mi (7,880.15 km) |
| Chicago to Isola Capo Rizzuto | 5,129.60 mi (8,255.29 km) |
| Chicago to Isola del Liri | 4,866.51 mi (7,831.89 km) |
| Chicago to Isola della Scala | 4,612.69 mi (7,423.42 km) |
| Chicago to Isola Vicentina | 4,614.69 mi (7,426.62 km) |
| Chicago to Ispica | 5,138.68 mi (8,269.90 km) |
| Chicago to Istrana | 4,637.68 mi (7,463.62 km) |
| Chicago to Itri | 4,882.22 mi (7,857.17 km) |
