| Winnetka to Rosolini | 5,130.70 mi (8,257.07 km) |
| Winnetka to Rossano | 5,073.85 mi (8,165.58 km) |
| Winnetka to Rottofreno | 4,554.29 mi (7,329.42 km) |
| Winnetka to Rovato | 4,551.06 mi (7,324.23 km) |
| Winnetka to Roverbella | 4,593.34 mi (7,392.27 km) |
| Winnetka to Rovereto | 4,578.78 mi (7,368.83 km) |
| Winnetka to Rovigo | 4,640.98 mi (7,468.93 km) |
| Winnetka to Rozzano | 4,525.35 mi (7,282.85 km) |
| Winnetka to Rubano | 4,625.78 mi (7,444.47 km) |
| Winnetka to Rubiera | 4,619.61 mi (7,434.54 km) |
| Winnetka to Ruffano | 5,118.70 mi (8,237.75 km) |
| Winnetka to Russi | 4,680.00 mi (7,531.74 km) |
| Winnetka to Rutigliano | 5,022.05 mi (8,082.20 km) |
| Winnetka to Ruvo di Puglia | 4,997.35 mi (8,042.46 km) |
| Winnetka to Sabaudia | 4,851.72 mi (7,808.09 km) |
