| Chicago to Robertsville (New Jersey) | 704.32 mi (1,133.50 km) |
| Chicago to Robinson (Texas) | 886.78 mi (1,427.13 km) |
| Chicago to Robstown (Texas) | 1,121.58 mi (1,805.01 km) |
| Chicago to Rochester (Michigan) | 240.74 mi (387.44 km) |
| Chicago to Rochester (Minnesota) | 285.24 mi (459.05 km) |
| Chicago to Rochester (New Hampshire) | 854.71 mi (1,375.52 km) |
| Chicago to Rochester (New York) | 520.81 mi (838.16 km) |
| Chicago to Rochester Hills (Michigan) | 238.60 mi (383.99 km) |
| Chicago to Rock Hill (South Carolina) | 597.24 mi (961.17 km) |
| Chicago to Rock Island (Illinois) | 151.64 mi (244.05 km) |
| Chicago to Rock Springs (Wyoming) | 1,107.84 mi (1,782.89 km) |
| Chicago to Rockford (Illinois) | 76.45 mi (123.04 km) |
| Chicago to Rockledge (Florida) | 1,012.36 mi (1,629.23 km) |
| Chicago to Rocklin (California) | 1,768.98 mi (2,846.90 km) |
| Chicago to Rockport (Texas) | 1,090.55 mi (1,755.08 km) |
