| Chesapeake to Yonkers (New York) | 322.73 mi (519.38 km) |
| Chesapeake to Yorba Linda (California) | 2,328.70 mi (3,747.69 km) |
| Chesapeake to York (Pennsylvania) | 228.32 mi (367.44 km) |
| Chesapeake to Yorktown (Indiana) | 553.82 mi (891.29 km) |
| Chesapeake to Yorkville (Illinois) | 735.12 mi (1,183.06 km) |
| Chesapeake to Youngstown (Ohio) | 384.47 mi (618.74 km) |
| Chesapeake to Youngsville (Louisiana) | 1,011.41 mi (1,627.71 km) |
| Chesapeake to Ypsilanti (Michigan) | 547.60 mi (881.28 km) |
| Chesapeake to Yuba City (California) | 2,451.62 mi (3,945.50 km) |
| Chesapeake to Yucaipa (California) | 2,285.84 mi (3,678.71 km) |
| Chesapeake to Yucca Valley (California) | 2,249.98 mi (3,620.99 km) |
| Chesapeake to Yukon (Oklahoma) | 1,198.31 mi (1,928.50 km) |
| Chesapeake to Yulee (Florida) | 515.56 mi (829.72 km) |
| Chesapeake to Yuma (Arizona) | 2,177.96 mi (3,505.09 km) |
| Chesapeake to Zachary (Louisiana) | 948.71 mi (1,526.80 km) |
