| Chicago to Redondela | 3,897.38 mi (6,272.22 km) |
| Chicago to Reinosa | 4,071.40 mi (6,552.29 km) |
| Chicago to Requena | 4,333.24 mi (6,973.68 km) |
| Chicago to Reus | 4,367.23 mi (7,028.37 km) |
| Chicago to Rianxo | 3,876.35 mi (6,238.39 km) |
| Chicago to Ribadeo | 3,926.14 mi (6,318.51 km) |
| Chicago to Rincon de la Victoria | 4,293.10 mi (6,909.07 km) |
| Chicago to Ripoll | 4,373.93 mi (7,039.16 km) |
| Chicago to Ripollet | 4,399.47 mi (7,080.26 km) |
| Chicago to Rojales | 4,403.60 mi (7,086.90 km) |
| Chicago to Ronda | 4,251.39 mi (6,841.95 km) |
| Chicago to Roquetas de Mar | 4,368.37 mi (7,030.21 km) |
| Chicago to Rosas | 4,413.45 mi (7,102.76 km) |
| Chicago to Rubi | 4,394.23 mi (7,071.83 km) |
| Chicago to Rute | 4,266.66 mi (6,866.52 km) |
