| Chicago to Ridgeland (Mississippi) | 664.33 mi (1,069.14 km) |
| Chicago to Ridgewood (New Jersey) | 705.14 mi (1,134.81 km) |
| Chicago to Rifle (Colorado) | 1,061.81 mi (1,708.81 km) |
| Chicago to Rincon (Georgia) | 748.60 mi (1,204.75 km) |
| Chicago to Ringwood (New Jersey) | 695.45 mi (1,119.22 km) |
| Chicago to Río Grande (Puerto Rico) | 2,068.52 mi (3,328.96 km) |
| Chicago to Rio Grande City (Texas) | 1,240.97 mi (1,997.15 km) |
| Chicago to Rio Linda (California) | 1,781.40 mi (2,866.89 km) |
| Chicago to Rio Rancho (New Mexico) | 1,119.23 mi (1,801.23 km) |
| Chicago to Rio Rico (Arizona) | 1,469.01 mi (2,364.14 km) |
| Chicago to Ripon (California) | 1,786.47 mi (2,875.05 km) |
| Chicago to River Edge (New Jersey) | 709.57 mi (1,141.94 km) |
| Chicago to River Falls (Wisconsin) | 324.23 mi (521.80 km) |
| Chicago to River Forest (Illinois) | 7.90 mi (12.72 km) |
| Chicago to River Grove (Illinois) | 9.83 mi (15.81 km) |
