| Chicago to Savannah (Georgia) | 766.46 mi (1,233.50 km) |
| Chicago to Sayreville (New Jersey) | 700.91 mi (1,128.00 km) |
| Chicago to Sayville (New York) | 760.87 mi (1,224.50 km) |
| Chicago to Scaggsville (Maryland) | 596.91 mi (960.64 km) |
| Chicago to Scarsdale (New York) | 722.31 mi (1,162.45 km) |
| Chicago to Schaumburg (Illinois) | 24.40 mi (39.26 km) |
| Chicago to Schenectady (New York) | 705.28 mi (1,135.03 km) |
| Chicago to Schererville (Indiana) | 27.31 mi (43.96 km) |
| Chicago to Schertz (Texas) | 1,032.84 mi (1,662.20 km) |
| Chicago to Schiller Park (Illinois) | 12.58 mi (20.25 km) |
| Chicago to Schofield Barracks (Hawaii) | 4,248.95 mi (6,838.02 km) |
| Chicago to Scotchtown (New York) | 687.36 mi (1,106.20 km) |
| Chicago to Scottdale (Georgia) | 586.11 mi (943.26 km) |
| Chicago to Scotts Valley (California) | 1,848.30 mi (2,974.55 km) |
| Chicago to Scottsbluff (Nebraska) | 820.96 mi (1,321.21 km) |
