| Chicago to Iselin (New Jersey) | 699.77 mi (1,126.16 km) |
| Chicago to Isla Vista (California) | 1,810.57 mi (2,913.83 km) |
| Chicago to Issaquah (Washington) | 1,718.14 mi (2,765.09 km) |
| Chicago to Ithaca (New York) | 574.07 mi (923.87 km) |
| Chicago to Ives Estates (Florida) | 1,176.98 mi (1,894.16 km) |
| Chicago to Jackson (Michigan) | 170.76 mi (274.81 km) |
| Chicago to Jackson (Mississippi) | 672.37 mi (1,082.08 km) |
| Chicago to Jackson (Missouri) | 325.30 mi (523.51 km) |
| Chicago to Jackson (Tennessee) | 431.70 mi (694.76 km) |
| Chicago to Jackson (Wyoming) | 1,174.84 mi (1,890.71 km) |
| Chicago to Jacksonville (Alabama) | 564.62 mi (908.66 km) |
| Chicago to Jacksonville (Arkansas) | 537.39 mi (864.85 km) |
| Chicago to Jacksonville (Florida) | 862.32 mi (1,387.76 km) |
| Chicago to Jacksonville (Illinois) | 197.33 mi (317.58 km) |
| Chicago to Jacksonville (North Carolina) | 742.54 mi (1,195.01 km) |
