| Chicago to Anderson (California) | 1,791.08 mi (2,882.46 km) |
| Chicago to Anderson (Indiana) | 159.53 mi (256.74 km) |
| Chicago to Anderson (South Carolina) | 574.57 mi (924.68 km) |
| Chicago to Anderson Creek (North Carolina) | 654.02 mi (1,052.55 km) |
| Chicago to Andover (Kansas) | 577.49 mi (929.38 km) |
| Chicago to Andover (Minnesota) | 368.07 mi (592.36 km) |
| Chicago to Andrews (Texas) | 1,047.98 mi (1,686.55 km) |
| Chicago to Angleton (Texas) | 976.42 mi (1,571.40 km) |
| Chicago to Ankeny (Iowa) | 304.86 mi (490.62 km) |
| Chicago to Ann Arbor (Michigan) | 205.15 mi (330.16 km) |
| Chicago to Anna (Texas) | 760.44 mi (1,223.80 km) |
| Chicago to Annandale (Virginia) | 589.75 mi (949.12 km) |
| Chicago to Annapolis (Maryland) | 620.22 mi (998.15 km) |
| Chicago to Annapolis Neck (Maryland) | 621.25 mi (999.80 km) |
| Chicago to Anniston (Alabama) | 573.40 mi (922.79 km) |
