| Chicago to Shelton (Connecticut) | 752.00 mi (1,210.23 km) |
| Chicago to Shelton (Washington) | 1,768.07 mi (2,845.43 km) |
| Chicago to Shenandoah (Louisiana) | 811.32 mi (1,305.69 km) |
| Chicago to Shepherdsville (Kentucky) | 286.45 mi (461.00 km) |
| Chicago to Sheridan (Wyoming) | 987.91 mi (1,589.89 km) |
| Chicago to Sherman (Texas) | 747.59 mi (1,203.12 km) |
| Chicago to Sherrelwood (Colorado) | 913.96 mi (1,470.88 km) |
| Chicago to Sherwood (Arkansas) | 541.03 mi (870.70 km) |
| Chicago to Sherwood (Oregon) | 1,761.59 mi (2,835.01 km) |
| Chicago to Shiloh (Illinois) | 255.58 mi (411.31 km) |
| Chicago to Shiloh (Ohio) | 228.30 mi (367.42 km) |
| Chicago to Shiloh (Pennsylvania) | 582.88 mi (938.05 km) |
| Chicago to Shirley (New York) | 771.07 mi (1,240.91 km) |
| Chicago to Shively (Kentucky) | 270.34 mi (435.06 km) |
| Chicago to Shoreline (Washington) | 1,732.05 mi (2,787.47 km) |
