| Chicago to Alderwood Manor (Washington) | 1,728.61 mi (2,781.92 km) |
| Chicago to Aldine (Texas) | 928.72 mi (1,494.63 km) |
| Chicago to Alexander City (Alabama) | 623.35 mi (1,003.19 km) |
| Chicago to Alexandria (Louisiana) | 775.11 mi (1,247.41 km) |
| Chicago to Alexandria (Minnesota) | 473.68 mi (762.31 km) |
| Chicago to Alexandria (Virginia) | 595.55 mi (958.45 km) |
| Chicago to Algonquin (Illinois) | 39.36 mi (63.35 km) |
| Chicago to Alhambra (California) | 1,732.51 mi (2,788.20 km) |
| Chicago to Alice (Texas) | 1,135.27 mi (1,827.03 km) |
| Chicago to Aliso Viejo (California) | 1,727.95 mi (2,780.86 km) |
| Chicago to Allen (Texas) | 777.87 mi (1,251.87 km) |
| Chicago to Allen Park (Michigan) | 231.46 mi (372.50 km) |
| Chicago to Allendale (Michigan) | 118.86 mi (191.29 km) |
| Chicago to Allentown (Pennsylvania) | 639.86 mi (1,029.75 km) |
| Chicago to Alliance (Ohio) | 346.40 mi (557.48 km) |
