| Chicago to Payson (Arizona) | 1,383.22 mi (2,226.07 km) |
| Chicago to Payson (Utah) | 1,257.45 mi (2,023.66 km) |
| Chicago to Peabody (Massachusetts) | 855.66 mi (1,377.05 km) |
| Chicago to Peachtree City (Georgia) | 607.66 mi (977.94 km) |
| Chicago to Peachtree Corners (Georgia) | 575.35 mi (925.94 km) |
| Chicago to Pearl (Mississippi) | 673.94 mi (1,084.60 km) |
| Chicago to Pearl City (Hawaii) | 4,247.32 mi (6,835.40 km) |
| Chicago to Pearl River (New York) | 709.83 mi (1,142.36 km) |
| Chicago to Pearland (Texas) | 949.46 mi (1,528.01 km) |
| Chicago to Pebble Creek (Florida) | 991.83 mi (1,596.20 km) |
| Chicago to Pecan Grove (Texas) | 955.91 mi (1,538.39 km) |
| Chicago to Pecos (Texas) | 1,133.11 mi (1,823.57 km) |
| Chicago to Peekskill (New York) | 711.81 mi (1,145.54 km) |
| Chicago to Pekin (Illinois) | 133.60 mi (215.01 km) |
| Chicago to Pelham (Alabama) | 591.28 mi (951.57 km) |
