| Winter Springs to Yonkers (New York) | 944.40 mi (1,519.86 km) |
| Winter Springs to Yorba Linda (California) | 2,173.39 mi (3,497.74 km) |
| Winter Springs to York (Pennsylvania) | 820.70 mi (1,320.79 km) |
| Winter Springs to Yorktown (Indiana) | 829.85 mi (1,335.51 km) |
| Winter Springs to Yorkville (Illinois) | 982.54 mi (1,581.24 km) |
| Winter Springs to Youngstown (Ohio) | 858.20 mi (1,381.14 km) |
| Winter Springs to Youngsville (Louisiana) | 652.75 mi (1,050.51 km) |
| Winter Springs to Ypsilanti (Michigan) | 945.75 mi (1,522.04 km) |
| Winter Springs to Yuba City (California) | 2,402.62 mi (3,866.64 km) |
| Winter Springs to Yucaipa (California) | 2,131.60 mi (3,430.48 km) |
| Winter Springs to Yucca Valley (California) | 2,096.08 mi (3,373.31 km) |
| Winter Springs to Yukon (Oklahoma) | 1,072.57 mi (1,726.13 km) |
| Winter Springs to Yulee (Florida) | 135.64 mi (218.30 km) |
| Winter Springs to Yuma (Arizona) | 1,988.48 mi (3,200.16 km) |
| Winter Springs to Zachary (Louisiana) | 609.14 mi (980.31 km) |
