| Chicago to Stephenville (Texas) | 881.58 mi (1,418.77 km) |
| Chicago to Sterling (Colorado) | 809.00 mi (1,301.97 km) |
| Chicago to Sterling (Illinois) | 103.48 mi (166.53 km) |
| Chicago to Sterling (Virginia) | 574.68 mi (924.86 km) |
| Chicago to Sterling Heights (Michigan) | 243.72 mi (392.24 km) |
| Chicago to Steubenville (Ohio) | 380.00 mi (611.55 km) |
| Chicago to Stevens Point (Wisconsin) | 208.02 mi (334.77 km) |
| Chicago to Stevenson Ranch (California) | 1,746.15 mi (2,810.16 km) |
| Chicago to Stillwater (Minnesota) | 340.60 mi (548.14 km) |
| Chicago to Stillwater (Oklahoma) | 639.35 mi (1,028.94 km) |
| Chicago to Stockbridge (Georgia) | 604.47 mi (972.81 km) |
| Chicago to Stockton (California) | 1,790.32 mi (2,881.24 km) |
| Chicago to Stone Ridge (Virginia) | 569.35 mi (916.28 km) |
| Chicago to Stonecrest (Georgia) | 595.62 mi (958.55 km) |
| Chicago to Stony Brook (New York) | 756.70 mi (1,217.79 km) |
