| Chicago to Punta Gorda (Florida) | 1,080.69 mi (1,739.20 km) |
| Chicago to Puyallup (Washington) | 1,729.52 mi (2,783.40 km) |
| Chicago to Queen Creek (Arizona) | 1,432.81 mi (2,305.89 km) |
| Chicago to Queens (New York) | 724.11 mi (1,165.35 km) |
| Chicago to Quincy (Illinois) | 233.47 mi (375.73 km) |
| Chicago to Quincy (Massachusetts) | 854.36 mi (1,374.95 km) |
| Chicago to Raceland (Louisiana) | 852.70 mi (1,372.28 km) |
| Chicago to Racine (Wisconsin) | 61.83 mi (99.50 km) |
| Chicago to Radcliff (Kentucky) | 292.66 mi (470.99 km) |
| Chicago to Radford (Virginia) | 500.28 mi (805.13 km) |
| Chicago to Rahway (New Jersey) | 701.12 mi (1,128.35 km) |
| Chicago to Raleigh (North Carolina) | 638.93 mi (1,028.26 km) |
| Chicago to Ramona (California) | 1,702.44 mi (2,739.82 km) |
| Chicago to Ramsey (Minnesota) | 373.00 mi (600.29 km) |
| Chicago to Ramsey (New Jersey) | 702.61 mi (1,130.74 km) |
