| Chicago to Indianola (Iowa) | 305.44 mi (491.55 km) |
| Chicago to Indio (California) | 1,647.11 mi (2,650.77 km) |
| Chicago to Inglewood (California) | 1,747.17 mi (2,811.80 km) |
| Chicago to Inkster (Michigan) | 226.42 mi (364.39 km) |
| Chicago to Inver Grove Heights (Minnesota) | 339.76 mi (546.78 km) |
| Chicago to Inwood (New York) | 728.20 mi (1,171.92 km) |
| Chicago to Iona (Florida) | 1,107.36 mi (1,782.13 km) |
| Chicago to Ionia (Michigan) | 154.86 mi (249.22 km) |
| Chicago to Iowa City (Iowa) | 198.52 mi (319.49 km) |
| Chicago to Irmo (South Carolina) | 640.38 mi (1,030.59 km) |
| Chicago to Irondale (Alabama) | 575.76 mi (926.59 km) |
| Chicago to Ironton (Ohio) | 349.24 mi (562.05 km) |
| Chicago to Irvine (California) | 1,727.05 mi (2,779.42 km) |
| Chicago to Irving (Texas) | 802.02 mi (1,290.73 km) |
| Chicago to Isabela (Puerto Rico) | 2,019.13 mi (3,249.48 km) |
