| Chicago to Hutchinson (Minnesota) | 396.40 mi (637.95 km) |
| Chicago to Hutto (Texas) | 953.25 mi (1,534.11 km) |
| Chicago to Hyattsville (Maryland) | 598.12 mi (962.59 km) |
| Chicago to Hybla Valley (Virginia) | 597.72 mi (961.94 km) |
| Chicago to Idaho Falls (Idaho) | 1,237.96 mi (1,992.30 km) |
| Chicago to Idylwood (Virginia) | 587.69 mi (945.79 km) |
| Chicago to Ilchester (Maryland) | 600.77 mi (966.84 km) |
| Chicago to Immokalee (Florida) | 1,122.64 mi (1,806.72 km) |
| Chicago to Imperial (California) | 1,643.96 mi (2,645.70 km) |
| Chicago to Imperial Beach (California) | 1,731.01 mi (2,785.79 km) |
| Chicago to Independence (Kentucky) | 258.86 mi (416.60 km) |
| Chicago to Independence (Missouri) | 398.35 mi (641.08 km) |
| Chicago to Indian Trail (North Carolina) | 602.70 mi (969.95 km) |
| Chicago to Indiana (Pennsylvania) | 451.00 mi (725.82 km) |
| Chicago to Indianapolis (Indiana) | 163.58 mi (263.25 km) |
