| Chicago to Southern Pines (North Carolina) | 640.70 mi (1,031.11 km) |
| Chicago to Southfield (Michigan) | 230.93 mi (371.65 km) |
| Chicago to Southgate (Michigan) | 231.37 mi (372.35 km) |
| Chicago to Southlake (Texas) | 803.02 mi (1,292.33 km) |
| Chicago to Spanaway (Washington) | 1,735.84 mi (2,793.56 km) |
| Chicago to Spanish Fork (Utah) | 1,251.18 mi (2,013.59 km) |
| Chicago to Spanish Lake (Missouri) | 249.02 mi (400.76 km) |
| Chicago to Spanish Springs (Nevada) | 1,671.20 mi (2,689.54 km) |
| Chicago to Sparks (Nevada) | 1,675.15 mi (2,695.90 km) |
| Chicago to Spartanburg (South Carolina) | 569.06 mi (915.81 km) |
| Chicago to Spearfish (South Dakota) | 831.77 mi (1,338.60 km) |
| Chicago to Speedway (Indiana) | 159.99 mi (257.48 km) |
| Chicago to Spencer (Iowa) | 390.87 mi (629.05 km) |
| Chicago to Spokane (Washington) | 1,503.80 mi (2,420.12 km) |
| Chicago to Spokane Valley (Washington) | 1,494.57 mi (2,405.27 km) |
