| Chicago to Timberwood Park (Texas) | 1,032.40 mi (1,661.49 km) |
| Chicago to Timonium (Maryland) | 603.62 mi (971.43 km) |
| Chicago to Tinley Park (Illinois) | 19.66 mi (31.64 km) |
| Chicago to Tinton Falls (New Jersey) | 715.61 mi (1,151.66 km) |
| Chicago to Tipp City (Ohio) | 223.93 mi (360.38 km) |
| Chicago to Titusville (Florida) | 994.26 mi (1,600.11 km) |
| Chicago to Toledo (Ohio) | 211.86 mi (340.96 km) |
| Chicago to Tomball (Texas) | 923.66 mi (1,486.49 km) |
| Chicago to Tonawanda (New York) | 456.16 mi (734.13 km) |
| Chicago to Tooele (Utah) | 1,278.97 mi (2,058.31 km) |
| Chicago to Topeka (Kansas) | 463.32 mi (745.64 km) |
| Chicago to Torrance (California) | 1,750.89 mi (2,817.79 km) |
| Chicago to Torrington (Connecticut) | 748.54 mi (1,204.66 km) |
| Chicago to Totowa (New Jersey) | 700.43 mi (1,127.24 km) |
| Chicago to Town 'n' Country (Florida) | 997.73 mi (1,605.70 km) |
