| Chicago to Hormigueros (Puerto Rico) | 2,036.44 mi (3,277.33 km) |
| Chicago to Horn Lake (Mississippi) | 492.65 mi (792.85 km) |
| Chicago to Hot Springs (Arkansas) | 585.08 mi (941.60 km) |
| Chicago to Hot Springs Village (Arkansas) | 572.58 mi (921.48 km) |
| Chicago to Houma (Louisiana) | 863.52 mi (1,389.70 km) |
| Chicago to Houston (Texas) | 936.87 mi (1,507.74 km) |
| Chicago to Howard (Wisconsin) | 189.92 mi (305.65 km) |
| Chicago to Huber Heights (Ohio) | 231.40 mi (372.40 km) |
| Chicago to Hudson (Florida) | 972.66 mi (1,565.35 km) |
| Chicago to Hudson (Ohio) | 325.57 mi (523.95 km) |
| Chicago to Hudson (Wisconsin) | 332.74 mi (535.49 km) |
| Chicago to Hueytown (Alabama) | 582.45 mi (937.37 km) |
| Chicago to Hugo (Minnesota) | 350.20 mi (563.60 km) |
| Chicago to Humacao (Puerto Rico) | 2,082.24 mi (3,351.04 km) |
| Chicago to Humble (Texas) | 920.85 mi (1,481.96 km) |
