| Chicago to Shoreview (Minnesota) | 353.42 mi (568.77 km) |
| Chicago to Shorewood (Illinois) | 35.12 mi (56.51 km) |
| Chicago to Shorewood (Wisconsin) | 87.23 mi (140.38 km) |
| Chicago to Short Hills (New Jersey) | 696.97 mi (1,121.66 km) |
| Chicago to Short Pump (Virginia) | 607.30 mi (977.35 km) |
| Chicago to Show Low (Arizona) | 1,318.79 mi (2,122.39 km) |
| Chicago to Shreveport (Louisiana) | 729.23 mi (1,173.59 km) |
| Chicago to Sicklerville (New Jersey) | 678.85 mi (1,092.51 km) |
| Chicago to Sidney (Ohio) | 212.27 mi (341.62 km) |
| Chicago to Sierra Madre (California) | 1,725.52 mi (2,776.95 km) |
| Chicago to Sierra Vista (Arizona) | 1,434.14 mi (2,308.03 km) |
| Chicago to Sierra Vista Southeast (Arizona) | 1,433.93 mi (2,307.68 km) |
| Chicago to Signal Hill (California) | 1,743.07 mi (2,805.20 km) |
| Chicago to Sikeston (Missouri) | 356.88 mi (574.35 km) |
| Chicago to Siloam Springs (Arkansas) | 535.93 mi (862.49 km) |
