| Chicago to Romeoville (Illinois) | 25.61 mi (41.21 km) |
| Chicago to Romulus (Michigan) | 223.32 mi (359.39 km) |
| Chicago to Ronkonkoma (New York) | 758.08 mi (1,220.02 km) |
| Chicago to Roosevelt (New York) | 736.02 mi (1,184.51 km) |
| Chicago to Rosamond (California) | 1,712.70 mi (2,756.33 km) |
| Chicago to Rosaryville (Maryland) | 609.77 mi (981.32 km) |
| Chicago to Roscoe (Illinois) | 78.98 mi (127.11 km) |
| Chicago to Rose Hill (Virginia) | 595.33 mi (958.09 km) |
| Chicago to Roseburg (Oregon) | 1,804.68 mi (2,904.35 km) |
| Chicago to Rosedale (California) | 1,748.26 mi (2,813.55 km) |
| Chicago to Rosedale (Maryland) | 611.17 mi (983.58 km) |
| Chicago to Roselle (Illinois) | 22.81 mi (36.70 km) |
| Chicago to Roselle (New Jersey) | 701.59 mi (1,129.09 km) |
| Chicago to Roselle Park (New Jersey) | 701.07 mi (1,128.27 km) |
| Chicago to Rosemead (California) | 1,730.27 mi (2,784.60 km) |
