| Chicago to Rancho Cordova (California) | 1,774.13 mi (2,855.18 km) |
| Chicago to Rancho Cucamonga (California) | 1,702.25 mi (2,739.50 km) |
| Chicago to Rancho Mirage (California) | 1,655.92 mi (2,664.94 km) |
| Chicago to Rancho Palos Verdes (California) | 1,754.53 mi (2,823.65 km) |
| Chicago to Rancho San Diego (California) | 1,714.35 mi (2,758.98 km) |
| Chicago to Rancho Santa Margarita (California) | 1,719.63 mi (2,767.48 km) |
| Chicago to Randallstown (Maryland) | 595.33 mi (958.09 km) |
| Chicago to Rantoul (Illinois) | 108.79 mi (175.07 km) |
| Chicago to Rapid City (South Dakota) | 799.28 mi (1,286.31 km) |
| Chicago to Ravenna (Ohio) | 336.66 mi (541.81 km) |
| Chicago to Raymondville (Texas) | 1,205.95 mi (1,940.80 km) |
| Chicago to Raymore (Missouri) | 413.60 mi (665.62 km) |
| Chicago to Raytown (Missouri) | 406.89 mi (654.82 km) |
| Chicago to Reading (Ohio) | 248.54 mi (399.98 km) |
| Chicago to Reading (Pennsylvania) | 620.56 mi (998.70 km) |
