| Chicago to Altus (Oklahoma) | 801.06 mi (1,289.18 km) |
| Chicago to Alum Rock (California) | 1,830.94 mi (2,946.62 km) |
| Chicago to Alvin (Texas) | 959.51 mi (1,544.19 km) |
| Chicago to Amarillo (Texas) | 889.99 mi (1,432.31 km) |
| Chicago to Amelia (Ohio) | 266.25 mi (428.49 km) |
| Chicago to American Canyon (California) | 1,834.42 mi (2,952.22 km) |
| Chicago to American Fork (Utah) | 1,255.00 mi (2,019.73 km) |
| Chicago to Americus (Georgia) | 701.00 mi (1,128.15 km) |
| Chicago to Ames (Iowa) | 305.29 mi (491.31 km) |
| Chicago to Amherst (Ohio) | 283.38 mi (456.06 km) |
| Chicago to Ammon (Idaho) | 1,234.03 mi (1,985.98 km) |
| Chicago to Amsterdam (New York) | 692.17 mi (1,113.93 km) |
| Chicago to Anacortes (Washington) | 1,746.48 mi (2,810.69 km) |
| Chicago to Anaheim (California) | 1,726.10 mi (2,777.90 km) |
| Chicago to Anchorage (Alaska) | 2,823.84 mi (4,544.53 km) |
