| Chicago to Watervliet (New York) | 716.43 mi (1,152.98 km) |
| Chicago to Watsonville (California) | 1,839.26 mi (2,960.00 km) |
| Chicago to Wauconda (Illinois) | 38.01 mi (61.17 km) |
| Chicago to Waukee (Iowa) | 320.13 mi (515.19 km) |
| Chicago to Waukegan (Illinois) | 37.98 mi (61.13 km) |
| Chicago to Waukesha (Wisconsin) | 85.81 mi (138.10 km) |
| Chicago to Waunakee (Wisconsin) | 129.07 mi (207.71 km) |
| Chicago to Waupun (Wisconsin) | 134.94 mi (217.17 km) |
| Chicago to Wausau (Wisconsin) | 237.21 mi (381.76 km) |
| Chicago to Wauwatosa (Wisconsin) | 86.42 mi (139.08 km) |
| Chicago to Waverly (Iowa) | 252.09 mi (405.71 km) |
| Chicago to Waverly (Michigan) | 167.95 mi (270.29 km) |
| Chicago to Waxahachie (Texas) | 823.21 mi (1,324.83 km) |
| Chicago to Waxhaw (North Carolina) | 606.78 mi (976.52 km) |
| Chicago to Waycross (Georgia) | 791.17 mi (1,273.27 km) |
