| Chicago to Silver Firs (Washington) | 1,723.22 mi (2,773.25 km) |
| Chicago to Silver Spring (Maryland) | 593.75 mi (955.55 km) |
| Chicago to Silver Springs Shores (Florida) | 934.75 mi (1,504.34 km) |
| Chicago to Silverdale (Washington) | 1,747.81 mi (2,812.83 km) |
| Chicago to Silverton (Oregon) | 1,760.76 mi (2,833.67 km) |
| Chicago to Simi Valley (California) | 1,758.15 mi (2,829.46 km) |
| Chicago to Simpsonville (South Carolina) | 572.38 mi (921.16 km) |
| Chicago to Sioux City (Iowa) | 447.83 mi (720.72 km) |
| Chicago to Sioux Falls (South Dakota) | 473.89 mi (762.65 km) |
| Chicago to Skokie (Illinois) | 13.99 mi (22.51 km) |
| Chicago to Sleepy Hollow (New York) | 716.31 mi (1,152.79 km) |
| Chicago to Slidell (Louisiana) | 806.41 mi (1,297.80 km) |
| Chicago to Smithfield (North Carolina) | 666.05 mi (1,071.91 km) |
| Chicago to Smithfield (Utah) | 1,238.56 mi (1,993.26 km) |
| Chicago to Smithville (Missouri) | 398.67 mi (641.60 km) |
