| Winona to Sunset (Florida) | 1,417.30 mi (2,280.93 km) |
| Winona to Superior (Colorado) | 747.74 mi (1,203.38 km) |
| Winona to Superior (Wisconsin) | 183.76 mi (295.73 km) |
| Winona to Surprise (Arizona) | 1,322.06 mi (2,127.65 km) |
| Winona to Susanville (California) | 1,493.83 mi (2,404.09 km) |
| Winona to Sussex (Wisconsin) | 183.66 mi (295.57 km) |
| Winona to Suwanee (Georgia) | 801.43 mi (1,289.78 km) |
| Winona to Swansea (Illinois) | 389.88 mi (627.45 km) |
| Winona to Sweetwater (Florida) | 1,412.14 mi (2,272.62 km) |
| Winona to Sweetwater (Texas) | 928.88 mi (1,494.89 km) |
| Winona to Sycamore (Illinois) | 207.12 mi (333.33 km) |
| Winona to Sylacauga (Alabama) | 805.48 mi (1,296.29 km) |
| Winona to Sylvania (Ohio) | 433.98 mi (698.42 km) |
| Winona to Syosset (New York) | 950.84 mi (1,530.22 km) |
| Winona to Syracuse (New York) | 779.45 mi (1,254.40 km) |
