| Chicago to Rosolini | 5,139.25 mi (8,270.82 km) |
| Chicago to Rossano | 5,083.29 mi (8,180.76 km) |
| Chicago to Rottofreno | 4,564.02 mi (7,345.08 km) |
| Chicago to Rovato | 4,560.98 mi (7,340.18 km) |
| Chicago to Roverbella | 4,603.28 mi (7,408.26 km) |
| Chicago to Rovereto | 4,588.90 mi (7,385.13 km) |
| Chicago to Rovigo | 4,651.00 mi (7,485.06 km) |
| Chicago to Rozzano | 4,535.11 mi (7,298.56 km) |
| Chicago to Rubano | 4,635.89 mi (7,460.74 km) |
| Chicago to Rubiera | 4,629.40 mi (7,450.30 km) |
| Chicago to Ruffano | 5,128.47 mi (8,253.47 km) |
| Chicago to Russi | 4,689.89 mi (7,547.65 km) |
| Chicago to Rutigliano | 5,031.82 mi (8,097.93 km) |
| Chicago to Ruvo di Puglia | 5,007.11 mi (8,058.16 km) |
| Chicago to Sabaudia | 4,861.02 mi (7,823.05 km) |
