| Chicago to Harrison (Wisconsin) | 165.65 mi (266.59 km) |
| Chicago to Harrisonburg (Virginia) | 521.12 mi (838.66 km) |
| Chicago to Hartford (Connecticut) | 771.79 mi (1,242.07 km) |
| Chicago to Hartford (Wisconsin) | 108.46 mi (174.55 km) |
| Chicago to Hartselle (Alabama) | 512.78 mi (825.24 km) |
| Chicago to Hartsville (Tennessee) | 385.06 mi (619.69 km) |
| Chicago to Harvey (Illinois) | 15.98 mi (25.72 km) |
| Chicago to Harvey (Louisiana) | 836.24 mi (1,345.81 km) |
| Chicago to Hasbrouck Heights (New Jersey) | 708.51 mi (1,140.24 km) |
| Chicago to Haslett (Michigan) | 179.36 mi (288.66 km) |
| Chicago to Hastings (Minnesota) | 327.81 mi (527.56 km) |
| Chicago to Hastings (Nebraska) | 562.48 mi (905.23 km) |
| Chicago to Hattiesburg (Mississippi) | 733.12 mi (1,179.84 km) |
| Chicago to Hauppauge (New York) | 753.43 mi (1,212.53 km) |
| Chicago to Havelock (North Carolina) | 754.41 mi (1,214.11 km) |
