| Chicago to Homer Glen (Illinois) | 21.06 mi (33.90 km) |
| Chicago to Homestead (Florida) | 1,204.15 mi (1,937.89 km) |
| Chicago to Homewood (Alabama) | 580.68 mi (934.51 km) |
| Chicago to Homewood (Illinois) | 19.28 mi (31.03 km) |
| Chicago to Homosassa Springs (Florida) | 945.11 mi (1,521.01 km) |
| Chicago to Honeygo (Maryland) | 613.35 mi (987.10 km) |
| Chicago to Honolulu (Hawaii) | 4,244.71 mi (6,831.20 km) |
| Chicago to Hoover (Alabama) | 586.58 mi (944.01 km) |
| Chicago to Hopatcong (New Jersey) | 677.31 mi (1,090.03 km) |
| Chicago to Hope Mills (North Carolina) | 668.89 mi (1,076.48 km) |
| Chicago to Hopewell (Virginia) | 635.60 mi (1,022.90 km) |
| Chicago to Hopkins (Minnesota) | 357.64 mi (575.56 km) |
| Chicago to Hopkinsville (Kentucky) | 345.61 mi (556.20 km) |
| Chicago to Horizon City (Texas) | 1,237.35 mi (1,991.32 km) |
| Chicago to Horizon West (Florida) | 986.40 mi (1,587.46 km) |
