| Chicago to Superior (Colorado) | 920.46 mi (1,481.33 km) |
| Chicago to Superior (Wisconsin) | 399.73 mi (643.30 km) |
| Chicago to Surprise (Arizona) | 1,458.80 mi (2,347.70 km) |
| Chicago to Susanville (California) | 1,705.89 mi (2,745.37 km) |
| Chicago to Sussex (Wisconsin) | 93.69 mi (150.78 km) |
| Chicago to Suwanee (Georgia) | 572.84 mi (921.89 km) |
| Chicago to Swansea (Illinois) | 257.46 mi (414.34 km) |
| Chicago to Sweetwater (Florida) | 1,185.12 mi (1,907.26 km) |
| Chicago to Sweetwater (Texas) | 951.91 mi (1,531.95 km) |
| Chicago to Sycamore (Illinois) | 52.34 mi (84.23 km) |
| Chicago to Sylacauga (Alabama) | 603.37 mi (971.03 km) |
| Chicago to Sylvania (Ohio) | 205.12 mi (330.11 km) |
| Chicago to Syosset (New York) | 738.51 mi (1,188.52 km) |
| Chicago to Syracuse (New York) | 593.93 mi (955.84 km) |
| Chicago to Syracuse (Utah) | 1,259.35 mi (2,026.73 km) |
