| Chicago to Temple Terrace (Florida) | 998.83 mi (1,607.46 km) |
| Chicago to Tenafly (New Jersey) | 714.08 mi (1,149.20 km) |
| Chicago to Terre Haute (Indiana) | 164.67 mi (265.00 km) |
| Chicago to Terrell (Texas) | 786.15 mi (1,265.18 km) |
| Chicago to Terrytown (Louisiana) | 834.96 mi (1,343.74 km) |
| Chicago to Terryville (New York) | 760.74 mi (1,224.29 km) |
| Chicago to Texarkana (Arkansas) | 674.91 mi (1,086.15 km) |
| Chicago to Texarkana (Texas) | 676.54 mi (1,088.79 km) |
| Chicago to Texas City (Texas) | 949.81 mi (1,528.57 km) |
| Chicago to The Acreage (Florida) | 1,122.26 mi (1,806.11 km) |
| Chicago to The Colony (Texas) | 786.56 mi (1,265.85 km) |
| Chicago to The Crossings (Florida) | 1,191.65 mi (1,917.78 km) |
| Chicago to The Dalles (Oregon) | 1,680.16 mi (2,703.95 km) |
| Chicago to The Hammocks (Florida) | 1,190.79 mi (1,916.39 km) |
| Chicago to The Hills (New Jersey) | 682.94 mi (1,099.09 km) |
