| Chicago to Saddlebrooke (Arizona) | 1,421.89 mi (2,288.30 km) |
| Chicago to Safety Harbor (Florida) | 995.98 mi (1,602.87 km) |
| Chicago to Saginaw (Michigan) | 219.14 mi (352.66 km) |
| Chicago to Saginaw (Texas) | 815.49 mi (1,312.41 km) |
| Chicago to Sahuarita (Arizona) | 1,450.52 mi (2,334.39 km) |
| Chicago to Saks (Alabama) | 570.24 mi (917.72 km) |
| Chicago to Salem (Massachusetts) | 859.31 mi (1,382.92 km) |
| Chicago to Salem (Ohio) | 360.23 mi (579.73 km) |
| Chicago to Salem (Oregon) | 1,773.15 mi (2,853.60 km) |
| Chicago to Salem (Virginia) | 513.56 mi (826.49 km) |
| Chicago to Salem Lakes (Wisconsin) | 53.38 mi (85.91 km) |
| Chicago to Salida (California) | 1,784.84 mi (2,872.43 km) |
| Chicago to Salina (Kansas) | 562.70 mi (905.58 km) |
| Chicago to Salinas (California) | 1,837.98 mi (2,957.94 km) |
| Chicago to Salisbury (Maryland) | 681.97 mi (1,097.52 km) |
