| Chicago to Smolyan | 5,297.77 mi (8,525.94 km) |
| Chicago to Sofia | 5,193.64 mi (8,358.36 km) |
| Chicago to Sopot | 5,247.61 mi (8,445.21 km) |
| Chicago to Sozopol | 5,364.19 mi (8,632.84 km) |
| Chicago to Sredets | 5,349.90 mi (8,609.83 km) |
| Chicago to Stamboliyski | 5,264.90 mi (8,473.03 km) |
| Chicago to Stara Zagora | 5,290.58 mi (8,514.36 km) |
| Chicago to Svilengrad | 5,343.19 mi (8,599.04 km) |
| Chicago to Svishtov | 5,221.95 mi (8,403.91 km) |
| Chicago to Targovishte | 5,283.48 mi (8,502.93 km) |
| Chicago to Teteven | 5,217.22 mi (8,396.31 km) |
| Chicago to Troyan | 5,235.06 mi (8,425.02 km) |
| Chicago to Tryavna | 5,263.94 mi (8,471.49 km) |
| Chicago to Tutrakan | 5,245.13 mi (8,441.23 km) |
| Chicago to Varna | 5,331.71 mi (8,580.55 km) |
