| Chicago to Roy (Utah) | 1,257.20 mi (2,023.27 km) |
| Chicago to Royal Kunia (Hawaii) | 4,251.09 mi (6,841.47 km) |
| Chicago to Royal Oak (Michigan) | 236.66 mi (380.86 km) |
| Chicago to Royal Palm Beach (Florida) | 1,127.96 mi (1,815.28 km) |
| Chicago to Royse City (Texas) | 773.21 mi (1,244.36 km) |
| Chicago to Ruskin (Florida) | 1,020.52 mi (1,642.36 km) |
| Chicago to Russellville (Alabama) | 506.60 mi (815.29 km) |
| Chicago to Russellville (Arkansas) | 540.35 mi (869.61 km) |
| Chicago to Ruston (Louisiana) | 697.91 mi (1,123.18 km) |
| Chicago to Rutherford (New Jersey) | 707.38 mi (1,138.42 km) |
| Chicago to Rutland (Vermont) | 755.50 mi (1,215.86 km) |
| Chicago to Sabana Grande (Puerto Rico) | 2,045.41 mi (3,291.77 km) |
| Chicago to Sachse (Texas) | 782.24 mi (1,258.89 km) |
| Chicago to Saco (Maine) | 881.01 mi (1,417.86 km) |
| Chicago to Sacramento (California) | 1,785.34 mi (2,873.22 km) |
