| Chicago to The Villages (Florida) | 948.97 mi (1,527.23 km) |
| Chicago to The Woodlands (Texas) | 915.98 mi (1,474.12 km) |
| Chicago to Thibodaux (Louisiana) | 850.15 mi (1,368.18 km) |
| Chicago to Thomasville (Georgia) | 787.20 mi (1,266.88 km) |
| Chicago to Thomasville (North Carolina) | 579.89 mi (933.24 km) |
| Chicago to Thonotosassa (Florida) | 1,000.11 mi (1,609.52 km) |
| Chicago to Thornton (Colorado) | 909.64 mi (1,463.92 km) |
| Chicago to Thousand Oaks (California) | 1,766.93 mi (2,843.60 km) |
| Chicago to Three Lakes (Florida) | 1,193.61 mi (1,920.93 km) |
| Chicago to Tiffin (Ohio) | 238.49 mi (383.82 km) |
| Chicago to Tifton (Georgia) | 752.87 mi (1,211.63 km) |
| Chicago to Tigard (Oregon) | 1,758.42 mi (2,829.90 km) |
| Chicago to Tillmans Corner (Alabama) | 778.24 mi (1,252.45 km) |
| Chicago to Timberlake (Virginia) | 546.86 mi (880.08 km) |
| Chicago to Timberlane (Louisiana) | 836.58 mi (1,346.34 km) |
