| Chicago to Seymour (Tennessee) | 462.47 mi (744.28 km) |
| Chicago to Shady Hills (Florida) | 972.04 mi (1,564.34 km) |
| Chicago to Shafter (California) | 1,745.45 mi (2,809.03 km) |
| Chicago to Shaker Heights (Ohio) | 317.73 mi (511.34 km) |
| Chicago to Shakopee (Minnesota) | 354.74 mi (570.91 km) |
| Chicago to Sharon (Pennsylvania) | 373.92 mi (601.76 km) |
| Chicago to Sharonville (Ohio) | 246.54 mi (396.76 km) |
| Chicago to Shasta Lake (California) | 1,791.36 mi (2,882.91 km) |
| Chicago to Shawnee (Kansas) | 422.05 mi (679.22 km) |
| Chicago to Shawnee (Oklahoma) | 671.39 mi (1,080.50 km) |
| Chicago to Sheboygan (Wisconsin) | 131.49 mi (211.61 km) |
| Chicago to Shelby (North Carolina) | 560.65 mi (902.28 km) |
| Chicago to Shelbyville (Indiana) | 187.84 mi (302.31 km) |
| Chicago to Shelbyville (Kentucky) | 282.53 mi (454.68 km) |
| Chicago to Shelbyville (Tennessee) | 442.99 mi (712.93 km) |
