| Chicago to Worthington (Ohio) | 271.51 mi (436.96 km) |
| Chicago to Wright (Florida) | 789.32 mi (1,270.28 km) |
| Chicago to Wyandanch (New York) | 746.47 mi (1,201.33 km) |
| Chicago to Wyandotte (Michigan) | 233.95 mi (376.51 km) |
| Chicago to Wylie (Texas) | 776.53 mi (1,249.70 km) |
| Chicago to Wyndham (Virginia) | 606.31 mi (975.77 km) |
| Chicago to Wyoming (Michigan) | 124.55 mi (200.44 km) |
| Chicago to Wyomissing (Pennsylvania) | 618.46 mi (995.32 km) |
| Chicago to Xenia (Ohio) | 246.09 mi (396.05 km) |
| Chicago to Yakima (Washington) | 1,647.68 mi (2,651.69 km) |
| Chicago to Yankton (South Dakota) | 500.53 mi (805.53 km) |
| Chicago to Yauco (Puerto Rico) | 2,051.88 mi (3,302.18 km) |
| Chicago to Yazoo City (Mississippi) | 637.81 mi (1,026.45 km) |
| Chicago to Yeadon (Pennsylvania) | 662.07 mi (1,065.50 km) |
| Chicago to Yelm (Washington) | 1,745.58 mi (2,809.25 km) |
