| Chicago to Anoka (Minnesota) | 368.51 mi (593.06 km) |
| Chicago to Ansonia (Connecticut) | 755.23 mi (1,215.42 km) |
| Chicago to Antelope (California) | 1,776.67 mi (2,859.28 km) |
| Chicago to Anthem (Arizona) | 1,436.12 mi (2,311.21 km) |
| Chicago to Antioch (California) | 1,815.21 mi (2,921.30 km) |
| Chicago to Antioch (Illinois) | 48.22 mi (77.60 km) |
| Chicago to Apache Junction (Arizona) | 1,423.26 mi (2,290.52 km) |
| Chicago to Apex (North Carolina) | 634.76 mi (1,021.56 km) |
| Chicago to Apollo Beach (Florida) | 1,017.18 mi (1,636.99 km) |
| Chicago to Apopka (Florida) | 971.05 mi (1,562.76 km) |
| Chicago to Apple Valley (California) | 1,671.36 mi (2,689.80 km) |
| Chicago to Apple Valley (Minnesota) | 342.32 mi (550.90 km) |
| Chicago to Appleton (Wisconsin) | 172.31 mi (277.31 km) |
| Chicago to Arbutus (Maryland) | 603.98 mi (972.01 km) |
| Chicago to Arcadia (California) | 1,725.93 mi (2,777.61 km) |
