| Chicago to Abilene (Texas) | 926.06 mi (1,490.35 km) |
| Chicago to Accokeek (Maryland) | 603.75 mi (971.65 km) |
| Chicago to Acworth (Georgia) | 562.04 mi (904.52 km) |
| Chicago to Ada (Oklahoma) | 689.07 mi (1,108.95 km) |
| Chicago to Addison (Illinois) | 17.78 mi (28.62 km) |
| Chicago to Addison (Texas) | 791.78 mi (1,274.24 km) |
| Chicago to Adelanto (California) | 1,681.62 mi (2,706.31 km) |
| Chicago to Adelphi (Maryland) | 596.55 mi (960.05 km) |
| Chicago to Adrian (Michigan) | 187.42 mi (301.62 km) |
| Chicago to Affton (Missouri) | 266.44 mi (428.79 km) |
| Chicago to Agoura Hills (California) | 1,762.33 mi (2,836.19 km) |
| Chicago to Aguadilla (Puerto Rico) | 2,018.05 mi (3,247.73 km) |
| Chicago to Aiken (South Carolina) | 659.60 mi (1,061.53 km) |
| Chicago to Akron (Ohio) | 323.40 mi (520.47 km) |
| Chicago to Alabaster (Alabama) | 597.30 mi (961.25 km) |
