| Winnetka to Rende | 5,066.48 mi (8,153.72 km) |
| Winnetka to Resana | 4,623.81 mi (7,441.30 km) |
| Winnetka to Rescaldina | 4,508.05 mi (7,255.01 km) |
| Winnetka to Rezzato | 4,565.61 mi (7,347.65 km) |
| Winnetka to Rho | 4,514.69 mi (7,265.69 km) |
| Winnetka to Ribera | 5,029.64 mi (8,094.42 km) |
| Winnetka to Riccione Marina | 4,720.09 mi (7,596.25 km) |
| Winnetka to Riesi | 5,073.48 mi (8,164.98 km) |
| Winnetka to Rieti | 4,796.93 mi (7,719.91 km) |
| Winnetka to Rignano Flaminio | 4,790.90 mi (7,710.21 km) |
| Winnetka to Rignano sull'Arno | 4,684.75 mi (7,539.37 km) |
| Winnetka to Rimini | 4,714.36 mi (7,587.03 km) |
| Winnetka to Rionero in Vulture | 4,974.17 mi (8,005.15 km) |
| Winnetka to Riposto | 5,099.33 mi (8,206.58 km) |
| Winnetka to Riva del Garda | 4,571.07 mi (7,356.43 km) |
