| Chicago to Storm Lake (Iowa) | 388.00 mi (624.42 km) |
| Chicago to Storrs (Connecticut) | 793.67 mi (1,277.29 km) |
| Chicago to Stoughton (Wisconsin) | 108.52 mi (174.65 km) |
| Chicago to Stow (Ohio) | 326.63 mi (525.67 km) |
| Chicago to Streamwood (Illinois) | 28.26 mi (45.47 km) |
| Chicago to Streator (Illinois) | 76.99 mi (123.91 km) |
| Chicago to Streetsboro (Ohio) | 330.45 mi (531.81 km) |
| Chicago to Strongsville (Ohio) | 304.75 mi (490.45 km) |
| Chicago to Stuart (Florida) | 1,095.66 mi (1,763.29 km) |
| Chicago to Stuarts Draft (Virginia) | 528.51 mi (850.55 km) |
| Chicago to Sturgis (Michigan) | 116.82 mi (188.01 km) |
| Chicago to Suamico (Wisconsin) | 194.27 mi (312.64 km) |
| Chicago to Sudley (Virginia) | 576.30 mi (927.46 km) |
| Chicago to Suffern (New York) | 702.21 mi (1,130.09 km) |
| Chicago to Suffolk (Virginia) | 688.68 mi (1,108.33 km) |
