| Chicago to Vinings (Georgia) | 578.30 mi (930.69 km) |
| Chicago to Virginia Beach (Virginia) | 714.67 mi (1,150.15 km) |
| Chicago to Visalia (California) | 1,728.72 mi (2,782.11 km) |
| Chicago to Vista (California) | 1,715.95 mi (2,761.55 km) |
| Chicago to Wabash (Indiana) | 119.93 mi (193.02 km) |
| Chicago to Waco (Texas) | 882.68 mi (1,420.53 km) |
| Chicago to Waconia (Minnesota) | 370.18 mi (595.75 km) |
| Chicago to Wade Hampton (South Carolina) | 561.01 mi (902.86 km) |
| Chicago to Wadsworth (Ohio) | 313.41 mi (504.38 km) |
| Chicago to Waggaman (Louisiana) | 834.40 mi (1,342.83 km) |
| Chicago to Wahiawa (Hawaii) | 4,246.38 mi (6,833.89 km) |
| Chicago to Waianae (Hawaii) | 4,256.34 mi (6,849.91 km) |
| Chicago to Waihee-Waiehu (Hawaii) | 4,192.98 mi (6,747.95 km) |
| Chicago to Wailuku (Hawaii) | 4,194.44 mi (6,750.30 km) |
| Chicago to Waimalu (Hawaii) | 4,246.68 mi (6,834.36 km) |
