| Chicago to St. George (Utah) | 1,413.89 mi (2,275.44 km) |
| Chicago to St. Helens (Oregon) | 1,757.82 mi (2,828.94 km) |
| Chicago to St. James (New York) | 755.80 mi (1,216.34 km) |
| Chicago to St. John (Indiana) | 29.47 mi (47.44 km) |
| Chicago to St. Joseph (Missouri) | 399.66 mi (643.20 km) |
| Chicago to St. Louis (Missouri) | 259.09 mi (416.97 km) |
| Chicago to St. Louis Park (Minnesota) | 356.91 mi (574.39 km) |
| Chicago to St. Marys (Georgia) | 837.32 mi (1,347.53 km) |
| Chicago to St. Marys (Pennsylvania) | 473.04 mi (761.29 km) |
| Chicago to St. Matthews (Kentucky) | 270.51 mi (435.34 km) |
| Chicago to St. Michael (Minnesota) | 380.02 mi (611.59 km) |
| Chicago to St. Paul (Minnesota) | 346.51 mi (557.65 km) |
| Chicago to St. Peter (Minnesota) | 360.48 mi (580.14 km) |
| Chicago to St. Peters (Missouri) | 261.14 mi (420.27 km) |
| Chicago to St. Petersburg (Florida) | 1,010.81 mi (1,626.75 km) |
