| Chicago to Security-Widefield (Colorado) | 920.71 mi (1,481.73 km) |
| Chicago to Sedalia (Missouri) | 363.66 mi (585.25 km) |
| Chicago to Sedro-Woolley (Washington) | 1,728.38 mi (2,781.56 km) |
| Chicago to Seguin (Texas) | 1,022.40 mi (1,645.40 km) |
| Chicago to Selden (New York) | 761.29 mi (1,225.17 km) |
| Chicago to Selma (Alabama) | 651.91 mi (1,049.14 km) |
| Chicago to Selma (California) | 1,737.14 mi (2,795.65 km) |
| Chicago to Selma (Texas) | 1,033.48 mi (1,663.23 km) |
| Chicago to Seminole (Florida) | 1,005.59 mi (1,618.34 km) |
| Chicago to Seven Hills (Ohio) | 312.17 mi (502.39 km) |
| Chicago to Seven Oaks (South Carolina) | 645.14 mi (1,038.25 km) |
| Chicago to Severn (Maryland) | 606.48 mi (976.03 km) |
| Chicago to Severna Park (Maryland) | 614.03 mi (988.19 km) |
| Chicago to Sevierville (Tennessee) | 466.89 mi (751.39 km) |
| Chicago to Seymour (Indiana) | 220.89 mi (355.48 km) |
