| Winnetka to Smolyan | 5,286.73 mi (8,508.18 km) |
| Winnetka to Sofia | 5,182.58 mi (8,340.55 km) |
| Winnetka to Sopot | 5,236.36 mi (8,427.10 km) |
| Winnetka to Sozopol | 5,352.57 mi (8,614.13 km) |
| Winnetka to Sredets | 5,338.36 mi (8,591.26 km) |
| Winnetka to Stamboliyski | 5,253.77 mi (8,455.13 km) |
| Winnetka to Stara Zagora | 5,279.24 mi (8,496.11 km) |
| Winnetka to Svilengrad | 5,331.90 mi (8,580.87 km) |
| Winnetka to Svishtov | 5,210.43 mi (8,385.37 km) |
| Winnetka to Targovishte | 5,271.85 mi (8,484.23 km) |
| Winnetka to Teteven | 5,205.98 mi (8,378.22 km) |
| Winnetka to Troyan | 5,223.77 mi (8,406.84 km) |
| Winnetka to Tryavna | 5,252.54 mi (8,453.15 km) |
| Winnetka to Tutrakan | 5,233.36 mi (8,422.28 km) |
| Winnetka to Varna | 5,319.91 mi (8,561.56 km) |
