| Chicago to Yonkers (New York) | 718.17 mi (1,155.78 km) |
| Chicago to Yorba Linda (California) | 1,720.13 mi (2,768.28 km) |
| Chicago to York (Pennsylvania) | 586.11 mi (943.25 km) |
| Chicago to Yorktown (Indiana) | 160.98 mi (259.08 km) |
| Chicago to Yorkville (Illinois) | 41.33 mi (66.52 km) |
| Chicago to Youngstown (Ohio) | 367.94 mi (592.14 km) |
| Chicago to Youngsville (Louisiana) | 845.97 mi (1,361.46 km) |
| Chicago to Ypsilanti (Michigan) | 210.49 mi (338.75 km) |
| Chicago to Yuba City (California) | 1,782.21 mi (2,868.19 km) |
| Chicago to Yucaipa (California) | 1,678.48 mi (2,701.25 km) |
| Chicago to Yucca Valley (California) | 1,644.05 mi (2,645.85 km) |
| Chicago to Yukon (Oklahoma) | 696.28 mi (1,120.55 km) |
| Chicago to Yulee (Florida) | 845.21 mi (1,360.23 km) |
| Chicago to Yuma (Arizona) | 1,601.30 mi (2,577.04 km) |
| Chicago to Zachary (Louisiana) | 795.73 mi (1,280.60 km) |
