| Chicago to Town and Country (Missouri) | 265.96 mi (428.03 km) |
| Chicago to Towson (Maryland) | 604.02 mi (972.07 km) |
| Chicago to Tracy (California) | 1,803.35 mi (2,902.20 km) |
| Chicago to Traverse City (Michigan) | 227.12 mi (365.52 km) |
| Chicago to Travilah (Maryland) | 581.10 mi (935.19 km) |
| Chicago to Trenton (Michigan) | 231.69 mi (372.87 km) |
| Chicago to Trenton (New Jersey) | 682.02 mi (1,097.61 km) |
| Chicago to Trenton (Ohio) | 234.74 mi (377.77 km) |
| Chicago to Triangle (Virginia) | 591.98 mi (952.69 km) |
| Chicago to Trinity (Florida) | 985.06 mi (1,585.31 km) |
| Chicago to Trophy Club (Texas) | 801.71 mi (1,290.22 km) |
| Chicago to Trotwood (Ohio) | 225.84 mi (363.46 km) |
| Chicago to Troutdale (Oregon) | 1,739.04 mi (2,798.72 km) |
| Chicago to Troy (Alabama) | 699.83 mi (1,126.27 km) |
| Chicago to Troy (Illinois) | 244.47 mi (393.44 km) |
