| Chicago to Orangevale (California) | 1,770.06 mi (2,848.63 km) |
| Chicago to Orchards (Washington) | 1,744.83 mi (2,808.04 km) |
| Chicago to Orcutt (California) | 1,825.70 mi (2,938.19 km) |
| Chicago to Oregon (Ohio) | 219.68 mi (353.53 km) |
| Chicago to Oregon (Wisconsin) | 114.89 mi (184.89 km) |
| Chicago to Oregon City (Oregon) | 1,749.58 mi (2,815.67 km) |
| Chicago to Orem (Utah) | 1,251.29 mi (2,013.75 km) |
| Chicago to Orinda (California) | 1,837.14 mi (2,956.60 km) |
| Chicago to Orland Park (Illinois) | 18.28 mi (29.42 km) |
| Chicago to Orlando (Florida) | 989.58 mi (1,592.57 km) |
| Chicago to Ormond Beach (Florida) | 941.34 mi (1,514.94 km) |
| Chicago to Oro Valley (Arizona) | 1,432.10 mi (2,304.74 km) |
| Chicago to Oroville (California) | 1,771.16 mi (2,850.41 km) |
| Chicago to Oshkosh (Wisconsin) | 157.34 mi (253.21 km) |
| Chicago to Oskaloosa (Iowa) | 258.81 mi (416.51 km) |
