| Chicago to Holiday (Florida) | 983.34 mi (1,582.53 km) |
| Chicago to Holiday City-Berkeley (New Jersey) | 711.30 mi (1,144.73 km) |
| Chicago to Holladay (Utah) | 1,252.32 mi (2,015.42 km) |
| Chicago to Holland (Michigan) | 103.52 mi (166.60 km) |
| Chicago to Hollins (Virginia) | 515.35 mi (829.38 km) |
| Chicago to Hollister (California) | 1,821.73 mi (2,931.80 km) |
| Chicago to Holly Hill (Florida) | 946.04 mi (1,522.50 km) |
| Chicago to Holly Springs (Georgia) | 557.72 mi (897.57 km) |
| Chicago to Holly Springs (North Carolina) | 639.58 mi (1,029.31 km) |
| Chicago to Hollywood (Florida) | 1,172.98 mi (1,887.73 km) |
| Chicago to Holmen (Wisconsin) | 233.47 mi (375.74 km) |
| Chicago to Holt (Michigan) | 170.71 mi (274.73 km) |
| Chicago to Holtsville (New York) | 762.09 mi (1,226.47 km) |
| Chicago to Holyoke (Massachusetts) | 771.66 mi (1,241.87 km) |
| Chicago to Home Gardens (California) | 1,707.26 mi (2,747.57 km) |
