| Chicago to Hicksville (New York) | 738.00 mi (1,187.69 km) |
| Chicago to Hidalgo (Texas) | 1,241.50 mi (1,998.00 km) |
| Chicago to High Point (North Carolina) | 577.65 mi (929.64 km) |
| Chicago to Highland (California) | 1,682.22 mi (2,707.28 km) |
| Chicago to Highland (Illinois) | 237.16 mi (381.68 km) |
| Chicago to Highland (Indiana) | 23.18 mi (37.31 km) |
| Chicago to Highland (Utah) | 1,254.29 mi (2,018.58 km) |
| Chicago to Highland City (Florida) | 1,012.89 mi (1,630.09 km) |
| Chicago to Highland Park (Illinois) | 24.66 mi (39.68 km) |
| Chicago to Highland Park (New Jersey) | 695.03 mi (1,118.54 km) |
| Chicago to Highland Springs (Virginia) | 624.64 mi (1,005.26 km) |
| Chicago to Highland Village (Texas) | 792.48 mi (1,275.37 km) |
| Chicago to Highlands Ranch (Colorado) | 917.67 mi (1,476.85 km) |
| Chicago to Hillcrest (California) | 1,735.80 mi (2,793.50 km) |
| Chicago to Hillcrest Heights (Maryland) | 601.04 mi (967.28 km) |
