| Chicago to Ickenham | 3,937.77 mi (6,337.23 km) |
| Chicago to Ifield | 3,960.92 mi (6,374.49 km) |
| Chicago to Ilford | 3,958.12 mi (6,369.98 km) |
| Chicago to Ilfracombe | 3,806.82 mi (6,126.48 km) |
| Chicago to Ilkeston | 3,861.30 mi (6,214.17 km) |
| Chicago to Ilkley | 3,813.75 mi (6,137.64 km) |
| Chicago to Immingham | 3,882.07 mi (6,247.59 km) |
| Chicago to Ince-in-Makerfield | 3,796.24 mi (6,109.46 km) |
| Chicago to Inverness | 3,631.05 mi (5,843.62 km) |
| Chicago to Inverurie | 3,699.90 mi (5,954.41 km) |
| Chicago to Ipswich | 3,982.24 mi (6,408.80 km) |
| Chicago to Irlam | 3,805.62 mi (6,124.55 km) |
| Chicago to Irthlingborough | 3,907.32 mi (6,288.23 km) |
| Chicago to Irvine | 3,663.07 mi (5,895.15 km) |
| Chicago to Islington | 3,951.39 mi (6,359.14 km) |
