| Chicago to Hilliard (Ohio) | 267.12 mi (429.89 km) |
| Chicago to Hillsboro (Oregon) | 1,765.18 mi (2,840.78 km) |
| Chicago to Hillsborough (California) | 1,853.96 mi (2,983.66 km) |
| Chicago to Hillsborough (New Jersey) | 683.43 mi (1,099.87 km) |
| Chicago to Hilo (Hawaii) | 4,171.60 mi (6,713.54 km) |
| Chicago to Hilton Head Island (South Carolina) | 768.00 mi (1,235.97 km) |
| Chicago to Hinesville (Georgia) | 768.50 mi (1,236.77 km) |
| Chicago to Hinsdale (Illinois) | 12.65 mi (20.36 km) |
| Chicago to Hobart (Indiana) | 30.91 mi (49.74 km) |
| Chicago to Hobbs (New Mexico) | 1,055.43 mi (1,698.55 km) |
| Chicago to Hobe Sound (Florida) | 1,105.82 mi (1,779.65 km) |
| Chicago to Hoboken (New Jersey) | 712.31 mi (1,146.35 km) |
| Chicago to Hockessin (Delaware) | 643.06 mi (1,034.90 km) |
| Chicago to Hoffman Estates (Illinois) | 28.36 mi (45.64 km) |
| Chicago to Holbrook (New York) | 761.01 mi (1,224.73 km) |
