| Chicago to San Diego (California) | 1,722.19 mi (2,771.60 km) |
| Chicago to San Diego Country Estates (California) | 1,699.23 mi (2,734.65 km) |
| Chicago to San Dimas (California) | 1,715.11 mi (2,760.20 km) |
| Chicago to San Fernando (California) | 1,741.48 mi (2,802.64 km) |
| Chicago to San Francisco (California) | 1,853.72 mi (2,983.27 km) |
| Chicago to San Gabriel (California) | 1,730.31 mi (2,784.66 km) |
| Chicago to San Germán (Puerto Rico) | 2,042.59 mi (3,287.23 km) |
| Chicago to San Jacinto (California) | 1,683.45 mi (2,709.26 km) |
| Chicago to San Jose (California) | 1,833.84 mi (2,951.28 km) |
| Chicago to San Juan (Puerto Rico) | 2,059.32 mi (3,314.16 km) |
| Chicago to San Juan (Texas) | 1,233.87 mi (1,985.72 km) |
| Chicago to San Juan Capistrano (California) | 1,726.72 mi (2,778.89 km) |
| Chicago to San Leandro (California) | 1,840.19 mi (2,961.51 km) |
| Chicago to San Lorenzo (California) | 1,839.62 mi (2,960.58 km) |
| Chicago to San Luis (Arizona) | 1,613.14 mi (2,596.10 km) |
