| Chicago to St. Simons (Georgia) | 814.83 mi (1,311.35 km) |
| Chicago to Stafford (Texas) | 951.33 mi (1,531.02 km) |
| Chicago to Stallings (North Carolina) | 600.05 mi (965.69 km) |
| Chicago to Stamford (Connecticut) | 732.35 mi (1,178.61 km) |
| Chicago to Stanford (California) | 1,847.28 mi (2,972.91 km) |
| Chicago to Stanton (California) | 1,734.27 mi (2,791.03 km) |
| Chicago to Star (Idaho) | 1,459.28 mi (2,348.48 km) |
| Chicago to Starkville (Mississippi) | 582.13 mi (936.84 km) |
| Chicago to State College (Pennsylvania) | 514.94 mi (828.71 km) |
| Chicago to Staten Island (New York) | 708.20 mi (1,139.73 km) |
| Chicago to Statesboro (Georgia) | 726.06 mi (1,168.48 km) |
| Chicago to Statesville (North Carolina) | 556.00 mi (894.79 km) |
| Chicago to Staunton (Virginia) | 522.14 mi (840.31 km) |
| Chicago to Steamboat Springs (Colorado) | 997.89 mi (1,605.95 km) |
| Chicago to Steiner Ranch (Texas) | 974.68 mi (1,568.60 km) |
