| Chicago to University Place (Washington) | 1,741.51 mi (2,802.70 km) |
| Chicago to Upland (California) | 1,707.24 mi (2,747.53 km) |
| Chicago to Upper Arlington (Ohio) | 271.44 mi (436.83 km) |
| Chicago to Upper Grand Lagoon (Florida) | 813.45 mi (1,309.13 km) |
| Chicago to Upper Montclair (New Jersey) | 702.22 mi (1,130.11 km) |
| Chicago to Urbana (Illinois) | 122.25 mi (196.74 km) |
| Chicago to Urbana (Maryland) | 569.41 mi (916.38 km) |
| Chicago to Urbana (Ohio) | 237.36 mi (381.99 km) |
| Chicago to Urbandale (Iowa) | 314.45 mi (506.06 km) |
| Chicago to Utica (New York) | 640.40 mi (1,030.63 km) |
| Chicago to Uvalde (Texas) | 1,103.43 mi (1,775.80 km) |
| Chicago to Vacaville (California) | 1,815.49 mi (2,921.76 km) |
| Chicago to Vadnais Heights (Minnesota) | 349.91 mi (563.13 km) |
| Chicago to Vail (Arizona) | 1,433.91 mi (2,307.66 km) |
| Chicago to Valdosta (Georgia) | 797.49 mi (1,283.43 km) |
