| Chicago to San Luis Obispo (California) | 1,826.87 mi (2,940.07 km) |
| Chicago to San Marcos (California) | 1,714.53 mi (2,759.26 km) |
| Chicago to San Marcos (Texas) | 1,004.67 mi (1,616.86 km) |
| Chicago to San Marino (California) | 1,730.17 mi (2,784.44 km) |
| Chicago to San Mateo (California) | 1,851.68 mi (2,980.00 km) |
| Chicago to San Pablo (California) | 1,843.67 mi (2,967.09 km) |
| Chicago to San Rafael (California) | 1,852.26 mi (2,980.92 km) |
| Chicago to San Ramon (California) | 1,827.42 mi (2,940.95 km) |
| Chicago to San Tan Valley (Arizona) | 1,432.54 mi (2,305.45 km) |
| Chicago to Sand Springs (Oklahoma) | 600.10 mi (965.76 km) |
| Chicago to Sandusky (Ohio) | 258.73 mi (416.38 km) |
| Chicago to Sandy (Oregon) | 1,733.66 mi (2,790.05 km) |
| Chicago to Sandy (Utah) | 1,255.02 mi (2,019.76 km) |
| Chicago to Sandy Springs (Georgia) | 574.94 mi (925.28 km) |
| Chicago to Sanford (Florida) | 970.56 mi (1,561.96 km) |
