| Chicago to Wayne (Michigan) | 222.59 mi (358.23 km) |
| Chicago to Waynesboro (Pennsylvania) | 547.44 mi (881.02 km) |
| Chicago to Waynesboro (Virginia) | 532.87 mi (857.57 km) |
| Chicago to Weatherford (Oklahoma) | 734.74 mi (1,182.45 km) |
| Chicago to Weatherford (Texas) | 836.17 mi (1,345.69 km) |
| Chicago to Webb City (Missouri) | 485.53 mi (781.39 km) |
| Chicago to Webster (Texas) | 946.10 mi (1,522.60 km) |
| Chicago to Webster Groves (Missouri) | 265.04 mi (426.55 km) |
| Chicago to Weddington (North Carolina) | 602.15 mi (969.07 km) |
| Chicago to Weigelstown (Pennsylvania) | 580.69 mi (934.52 km) |
| Chicago to Weirton (West Virginia) | 383.40 mi (617.03 km) |
| Chicago to Wekiwa Springs (Florida) | 973.40 mi (1,566.53 km) |
| Chicago to Welby (Colorado) | 912.09 mi (1,467.87 km) |
| Chicago to Wellington (Colorado) | 901.29 mi (1,450.49 km) |
| Chicago to Wellington (Florida) | 1,130.74 mi (1,819.74 km) |
