| Winnetka to Imola | 4,668.54 mi (7,513.29 km) |
| Winnetka to Impruneta | 4,678.52 mi (7,529.35 km) |
| Winnetka to Induno Olona | 4,494.08 mi (7,232.52 km) |
| Winnetka to Inverigo | 4,513.78 mi (7,264.23 km) |
| Winnetka to Inveruno | 4,508.17 mi (7,255.19 km) |
| Winnetka to Inzago | 4,532.32 mi (7,294.07 km) |
| Winnetka to Iseo | 4,549.45 mi (7,321.64 km) |
| Winnetka to Isernia | 4,886.96 mi (7,864.80 km) |
| Winnetka to Isola Capo Rizzuto | 5,120.23 mi (8,240.22 km) |
| Winnetka to Isola del Liri | 4,857.04 mi (7,816.66 km) |
| Winnetka to Isola della Scala | 4,602.72 mi (7,407.37 km) |
| Winnetka to Isola Vicentina | 4,604.57 mi (7,410.34 km) |
| Winnetka to Ispica | 5,130.14 mi (8,256.16 km) |
| Winnetka to Istrana | 4,627.47 mi (7,447.19 km) |
| Winnetka to Itri | 4,872.85 mi (7,842.10 km) |
