| Chicago to Reidsville (North Carolina) | 573.22 mi (922.51 km) |
| Chicago to Reisterstown (Maryland) | 592.81 mi (954.03 km) |
| Chicago to Rendon (Texas) | 826.70 mi (1,330.44 km) |
| Chicago to Reno (Nevada) | 1,682.38 mi (2,707.52 km) |
| Chicago to Renton (Washington) | 1,724.87 mi (2,775.91 km) |
| Chicago to Republic (Missouri) | 446.30 mi (718.24 km) |
| Chicago to Reston (Virginia) | 579.11 mi (931.98 km) |
| Chicago to Revere (Massachusetts) | 854.43 mi (1,375.07 km) |
| Chicago to Rexburg (Idaho) | 1,224.73 mi (1,971.01 km) |
| Chicago to Reynoldsburg (Ohio) | 286.52 mi (461.12 km) |
| Chicago to Rialto (California) | 1,693.44 mi (2,725.32 km) |
| Chicago to Richardson (Texas) | 786.73 mi (1,266.12 km) |
| Chicago to Richfield (Minnesota) | 350.75 mi (564.48 km) |
| Chicago to Richfield (Wisconsin) | 100.75 mi (162.14 km) |
| Chicago to Richland (Washington) | 1,588.06 mi (2,555.73 km) |
