| Chicago to Hazleton (Pennsylvania) | 609.77 mi (981.34 km) |
| Chicago to Healdsburg (California) | 1,855.83 mi (2,986.67 km) |
| Chicago to Heath (Ohio) | 301.04 mi (484.48 km) |
| Chicago to Heber (Utah) | 1,232.73 mi (1,983.88 km) |
| Chicago to Helena (Alabama) | 592.65 mi (953.78 km) |
| Chicago to Helena (Montana) | 1,243.47 mi (2,001.18 km) |
| Chicago to Hemet (California) | 1,685.76 mi (2,712.97 km) |
| Chicago to Henderson (Kentucky) | 276.28 mi (444.63 km) |
| Chicago to Henderson (Nevada) | 1,517.08 mi (2,441.51 km) |
| Chicago to Henderson (North Carolina) | 625.72 mi (1,007.00 km) |
| Chicago to Henderson (Texas) | 774.70 mi (1,246.76 km) |
| Chicago to Hendersonville (North Carolina) | 531.03 mi (854.60 km) |
| Chicago to Hendersonville (Tennessee) | 386.58 mi (622.14 km) |
| Chicago to Hercules (California) | 1,838.24 mi (2,958.36 km) |
| Chicago to Hereford (Texas) | 931.27 mi (1,498.73 km) |
