| Chicago to Laguna Beach (California) | 1,730.69 mi (2,785.28 km) |
| Chicago to Laguna Hills (California) | 1,726.02 mi (2,777.77 km) |
| Chicago to Laguna Niguel (California) | 1,728.42 mi (2,781.62 km) |
| Chicago to Laguna Woods (California) | 1,727.00 mi (2,779.34 km) |
| Chicago to Lahaina (Hawaii) | 4,202.40 mi (6,763.10 km) |
| Chicago to Lake Arbor (Maryland) | 605.65 mi (974.70 km) |
| Chicago to Lake Barcroft (Virginia) | 591.10 mi (951.28 km) |
| Chicago to Lake Butler (Florida) | 984.83 mi (1,584.93 km) |
| Chicago to Lake Charles (Louisiana) | 860.73 mi (1,385.22 km) |
| Chicago to Lake City (Florida) | 852.19 mi (1,371.47 km) |
| Chicago to Lake Elmo (Minnesota) | 340.64 mi (548.20 km) |
| Chicago to Lake Elsinore (California) | 1,704.49 mi (2,743.11 km) |
| Chicago to Lake Forest (California) | 1,722.39 mi (2,771.92 km) |
| Chicago to Lake Forest (Illinois) | 29.06 mi (46.77 km) |
| Chicago to Lake Forest Park (Washington) | 1,729.44 mi (2,783.27 km) |
