| Chicago to Sanford (Maine) | 866.02 mi (1,393.72 km) |
| Chicago to Sanford (North Carolina) | 634.42 mi (1,021.00 km) |
| Chicago to Sanger (California) | 1,730.94 mi (2,785.67 km) |
| Chicago to Santa Ana (California) | 1,730.63 mi (2,785.18 km) |
| Chicago to Santa Barbara (California) | 1,802.86 mi (2,901.42 km) |
| Chicago to Santa Clara (California) | 1,838.48 mi (2,958.74 km) |
| Chicago to Santa Clara (Oregon) | 1,784.92 mi (2,872.55 km) |
| Chicago to Santa Clarita (California) | 1,740.59 mi (2,801.21 km) |
| Chicago to Santa Cruz (California) | 1,851.38 mi (2,979.50 km) |
| Chicago to Santa Fe (New Mexico) | 1,071.42 mi (1,724.28 km) |
| Chicago to Santa Fe (Texas) | 954.67 mi (1,536.39 km) |
| Chicago to Santa Fe Springs (California) | 1,733.56 mi (2,789.89 km) |
| Chicago to Santa Maria (California) | 1,824.90 mi (2,936.89 km) |
| Chicago to Santa Monica (California) | 1,752.03 mi (2,819.61 km) |
| Chicago to Santa Paula (California) | 1,771.62 mi (2,851.14 km) |
