| Chicago to Winder (Georgia) | 583.40 mi (938.90 km) |
| Chicago to Windsor (California) | 1,854.68 mi (2,984.82 km) |
| Chicago to Windsor (Colorado) | 899.98 mi (1,448.38 km) |
| Chicago to Winfield (Kansas) | 585.09 mi (941.61 km) |
| Chicago to Winnetka (Illinois) | 18.80 mi (30.25 km) |
| Chicago to Winona (Minnesota) | 252.81 mi (406.85 km) |
| Chicago to Winston-Salem (North Carolina) | 561.80 mi (904.14 km) |
| Chicago to Winter Garden (Florida) | 980.18 mi (1,577.45 km) |
| Chicago to Winter Gardens (California) | 1,712.12 mi (2,755.40 km) |
| Chicago to Winter Haven (Florida) | 1,012.96 mi (1,630.19 km) |
| Chicago to Winter Park (Florida) | 981.52 mi (1,579.60 km) |
| Chicago to Winter Springs (Florida) | 977.18 mi (1,572.62 km) |
| Chicago to Winterville (North Carolina) | 704.67 mi (1,134.06 km) |
| Chicago to Winton (California) | 1,768.47 mi (2,846.07 km) |
| Chicago to Wisconsin Rapids (Wisconsin) | 206.91 mi (332.98 km) |
