| Chicago to Woodlawn (Virginia) | 596.55 mi (960.05 km) |
| Chicago to Woodlyn (Pennsylvania) | 658.42 mi (1,059.62 km) |
| Chicago to Woodmere (Louisiana) | 838.94 mi (1,350.14 km) |
| Chicago to Woodmere (New York) | 729.47 mi (1,173.96 km) |
| Chicago to Woodridge (Illinois) | 19.53 mi (31.43 km) |
| Chicago to Woods Cross (Utah) | 1,254.26 mi (2,018.54 km) |
| Chicago to Woodstock (Georgia) | 561.64 mi (903.87 km) |
| Chicago to Woodstock (Illinois) | 50.38 mi (81.08 km) |
| Chicago to Woodward (Oklahoma) | 730.04 mi (1,174.88 km) |
| Chicago to Woonsocket (Rhode Island) | 831.05 mi (1,337.44 km) |
| Chicago to Wooster (Ohio) | 306.64 mi (493.49 km) |
| Chicago to Worcester (Massachusetts) | 813.99 mi (1,309.99 km) |
| Chicago to World Golf Village (Florida) | 889.95 mi (1,432.23 km) |
| Chicago to Worth (Illinois) | 11.68 mi (18.80 km) |
| Chicago to Worthington (Minnesota) | 419.99 mi (675.91 km) |
