| Chicago to Hermiston (Oregon) | 1,588.13 mi (2,555.84 km) |
| Chicago to Hermitage (Pennsylvania) | 376.96 mi (606.65 km) |
| Chicago to Hermosa Beach (California) | 1,752.70 mi (2,820.70 km) |
| Chicago to Hernando (Mississippi) | 498.64 mi (802.48 km) |
| Chicago to Herndon (Virginia) | 576.55 mi (927.87 km) |
| Chicago to Herriman (Utah) | 1,264.74 mi (2,035.40 km) |
| Chicago to Herrin (Illinois) | 288.04 mi (463.55 km) |
| Chicago to Hershey (Pennsylvania) | 584.75 mi (941.06 km) |
| Chicago to Hesperia (California) | 1,680.90 mi (2,705.14 km) |
| Chicago to Hewitt (Texas) | 889.13 mi (1,430.92 km) |
| Chicago to Hialeah (Florida) | 1,180.60 mi (1,899.99 km) |
| Chicago to Hialeah Gardens (Florida) | 1,178.35 mi (1,896.38 km) |
| Chicago to Hibbing (Minnesota) | 462.98 mi (745.09 km) |
| Chicago to Hickory (North Carolina) | 542.71 mi (873.41 km) |
| Chicago to Hickory Hills (Illinois) | 10.66 mi (17.16 km) |
