| Chicago Ridge to Smolyan | 5,307.70 mi (8,541.91 km) |
| Chicago Ridge to Sofia | 5,203.57 mi (8,374.33 km) |
| Chicago Ridge to Sopot | 5,257.58 mi (8,461.25 km) |
| Chicago Ridge to Sozopol | 5,374.23 mi (8,648.99 km) |
| Chicago Ridge to Sredets | 5,359.92 mi (8,625.96 km) |
| Chicago Ridge to Stamboliyski | 5,274.84 mi (8,489.03 km) |
| Chicago Ridge to Stara Zagora | 5,300.56 mi (8,530.43 km) |
| Chicago Ridge to Svilengrad | 5,353.17 mi (8,615.09 km) |
| Chicago Ridge to Svishtov | 5,231.97 mi (8,420.04 km) |
| Chicago Ridge to Targovishte | 5,293.52 mi (8,519.09 km) |
| Chicago Ridge to Teteven | 5,227.18 mi (8,412.34 km) |
| Chicago Ridge to Troyan | 5,245.04 mi (8,441.07 km) |
| Chicago Ridge to Tryavna | 5,273.94 mi (8,487.58 km) |
| Chicago Ridge to Tutrakan | 5,255.20 mi (8,457.43 km) |
| Chicago Ridge to Varna | 5,341.78 mi (8,596.76 km) |
