| Chicago to Haines City (Florida) | 1,008.11 mi (1,622.40 km) |
| Chicago to Halawa (Hawaii) | 4,246.52 mi (6,834.11 km) |
| Chicago to Half Moon Bay (California) | 1,860.17 mi (2,993.65 km) |
| Chicago to Halfway (Maryland) | 541.07 mi (870.77 km) |
| Chicago to Hallandale Beach (Florida) | 1,176.37 mi (1,893.19 km) |
| Chicago to Haltom City (Texas) | 814.77 mi (1,311.25 km) |
| Chicago to Ham Lake (Minnesota) | 363.28 mi (584.65 km) |
| Chicago to Hamilton (Ohio) | 235.14 mi (378.42 km) |
| Chicago to Hamilton Square (New Jersey) | 687.72 mi (1,106.78 km) |
| Chicago to Hammond (Indiana) | 18.29 mi (29.43 km) |
| Chicago to Hammond (Louisiana) | 797.89 mi (1,284.08 km) |
| Chicago to Hammonton (New Jersey) | 692.08 mi (1,113.80 km) |
| Chicago to Hampton (Virginia) | 687.81 mi (1,106.93 km) |
| Chicago to Hampton Bays (New York) | 788.29 mi (1,268.63 km) |
| Chicago to Hamtramck (Michigan) | 240.41 mi (386.91 km) |
