| Chicago to Arroyo Grande (California) | 1,826.62 mi (2,939.67 km) |
| Chicago to Artesia (California) | 1,736.55 mi (2,794.70 km) |
| Chicago to Artesia (New Mexico) | 1,106.43 mi (1,780.63 km) |
| Chicago to Artondale (Washington) | 1,745.89 mi (2,809.74 km) |
| Chicago to Arvada (Colorado) | 921.77 mi (1,483.45 km) |
| Chicago to Arvin (California) | 1,734.58 mi (2,791.53 km) |
| Chicago to Asbury Lake (Florida) | 878.39 mi (1,413.63 km) |
| Chicago to Asbury Park (New Jersey) | 720.63 mi (1,159.74 km) |
| Chicago to Ashburn (Virginia) | 570.79 mi (918.60 km) |
| Chicago to Asheboro (North Carolina) | 598.47 mi (963.15 km) |
| Chicago to Asheville (North Carolina) | 513.65 mi (826.64 km) |
| Chicago to Ashland (California) | 1,838.24 mi (2,958.36 km) |
| Chicago to Ashland (Kentucky) | 353.98 mi (569.68 km) |
| Chicago to Ashland (Ohio) | 286.48 mi (461.04 km) |
| Chicago to Ashland (Oregon) | 1,784.77 mi (2,872.30 km) |
