| Chicago to Plattsburgh (New York) | 741.58 mi (1,193.46 km) |
| Chicago to Pleasant Grove (Utah) | 1,252.32 mi (2,015.42 km) |
| Chicago to Pleasant Hill (California) | 1,830.16 mi (2,945.36 km) |
| Chicago to Pleasant Hill (Iowa) | 300.04 mi (482.87 km) |
| Chicago to Pleasant Prairie (Wisconsin) | 48.73 mi (78.43 km) |
| Chicago to Pleasant View (Utah) | 1,252.94 mi (2,016.41 km) |
| Chicago to Pleasanton (California) | 1,826.79 mi (2,939.93 km) |
| Chicago to Pleasanton (Texas) | 1,075.84 mi (1,731.39 km) |
| Chicago to Pleasantville (New Jersey) | 710.36 mi (1,143.21 km) |
| Chicago to Plover (Wisconsin) | 203.90 mi (328.15 km) |
| Chicago to Plum (Pennsylvania) | 422.83 mi (680.47 km) |
| Chicago to Plymouth (Indiana) | 78.35 mi (126.09 km) |
| Chicago to Plymouth (Minnesota) | 363.71 mi (585.33 km) |
| Chicago to Pocatello (Idaho) | 1,262.59 mi (2,031.95 km) |
| Chicago to Poinciana (Florida) | 1,009.93 mi (1,625.32 km) |
