| Chicago to Sestu | 4,784.15 mi (7,699.35 km) |
| Chicago to Settimo Torinese | 4,490.27 mi (7,226.39 km) |
| Chicago to Seveso | 4,524.14 mi (7,280.90 km) |
| Chicago to Sezze | 4,854.01 mi (7,811.77 km) |
| Chicago to Siano | 4,950.02 mi (7,966.28 km) |
| Chicago to Siena | 4,706.72 mi (7,574.73 km) |
| Chicago to Signa | 4,677.99 mi (7,528.50 km) |
| Chicago to Silea | 4,646.43 mi (7,477.71 km) |
| Chicago to Silvi Paese | 4,850.13 mi (7,805.53 km) |
| Chicago to Sinalunga | 4,727.01 mi (7,607.39 km) |
| Chicago to Siniscola | 4,755.70 mi (7,653.56 km) |
| Chicago to Sinnai | 4,788.72 mi (7,706.71 km) |
| Chicago to Siracusa | 5,141.85 mi (8,275.02 km) |
| Chicago to Solaro | 4,523.18 mi (7,279.36 km) |
| Chicago to Soliera | 4,631.30 mi (7,453.36 km) |
