| Chicago to Wichita (Kansas) | 587.05 mi (944.77 km) |
| Chicago to Wichita Falls (Texas) | 804.96 mi (1,295.46 km) |
| Chicago to Wickliffe (Ohio) | 320.96 mi (516.54 km) |
| Chicago to Wildomar (California) | 1,702.81 mi (2,740.41 km) |
| Chicago to Wildwood (Florida) | 957.04 mi (1,540.21 km) |
| Chicago to Wildwood (Missouri) | 274.61 mi (441.95 km) |
| Chicago to Wilkes-Barre (Pennsylvania) | 611.65 mi (984.36 km) |
| Chicago to Wilkinsburg (Pennsylvania) | 417.63 mi (672.12 km) |
| Chicago to Williamsburg (Virginia) | 663.88 mi (1,068.41 km) |
| Chicago to Williamsport (Pennsylvania) | 551.95 mi (888.28 km) |
| Chicago to Williamstown (New Jersey) | 680.74 mi (1,095.55 km) |
| Chicago to Willimantic (Connecticut) | 796.33 mi (1,281.57 km) |
| Chicago to Williston (North Dakota) | 891.46 mi (1,434.67 km) |
| Chicago to Willmar (Minnesota) | 433.36 mi (697.43 km) |
| Chicago to Willoughby (Ohio) | 323.87 mi (521.21 km) |
