| Chicago to Rockville (Maryland) | 584.95 mi (941.38 km) |
| Chicago to Rockville Centre (New York) | 733.41 mi (1,180.31 km) |
| Chicago to Rockwall (Texas) | 780.57 mi (1,256.21 km) |
| Chicago to Rocky Mount (North Carolina) | 667.68 mi (1,074.52 km) |
| Chicago to Rocky Point (New York) | 766.21 mi (1,233.10 km) |
| Chicago to Rocky River (Ohio) | 302.19 mi (486.33 km) |
| Chicago to Roessleville (New York) | 711.88 mi (1,145.65 km) |
| Chicago to Rogers (Arkansas) | 515.23 mi (829.18 km) |
| Chicago to Rogers (Minnesota) | 374.93 mi (603.39 km) |
| Chicago to Rohnert Park (California) | 1,853.17 mi (2,982.40 km) |
| Chicago to Rolla (Missouri) | 344.79 mi (554.89 km) |
| Chicago to Rolling Meadows (Illinois) | 23.90 mi (38.47 km) |
| Chicago to Roma (Texas) | 1,244.16 mi (2,002.28 km) |
| Chicago to Rome (Georgia) | 540.45 mi (869.77 km) |
| Chicago to Rome (New York) | 627.73 mi (1,010.23 km) |
