| Chicago to Rosemont (California) | 1,779.95 mi (2,864.55 km) |
| Chicago to Rosemount (Minnesota) | 336.91 mi (542.21 km) |
| Chicago to Rosenberg (Texas) | 963.10 mi (1,549.95 km) |
| Chicago to Roseville (California) | 1,773.39 mi (2,854.00 km) |
| Chicago to Roseville (Michigan) | 247.55 mi (398.39 km) |
| Chicago to Roseville (Minnesota) | 351.28 mi (565.33 km) |
| Chicago to Rossmoor (California) | 1,739.06 mi (2,798.74 km) |
| Chicago to Rossville (Maryland) | 612.04 mi (984.98 km) |
| Chicago to Roswell (Georgia) | 568.51 mi (914.94 km) |
| Chicago to Roswell (New Mexico) | 1,088.77 mi (1,752.21 km) |
| Chicago to Round Lake (Illinois) | 41.04 mi (66.05 km) |
| Chicago to Round Lake Beach (Illinois) | 42.54 mi (68.45 km) |
| Chicago to Round Rock (Texas) | 957.83 mi (1,541.47 km) |
| Chicago to Rowland Heights (California) | 1,723.61 mi (2,773.87 km) |
| Chicago to Rowlett (Texas) | 784.41 mi (1,262.38 km) |
