| Chicago to Popovo | 5,266.22 mi (8,475.17 km) |
| Chicago to Provadia | 5,316.56 mi (8,556.17 km) |
| Chicago to Radnevo | 5,307.29 mi (8,541.26 km) |
| Chicago to Radomir | 5,186.91 mi (8,347.52 km) |
| Chicago to Rakitovo | 5,255.75 mi (8,458.32 km) |
| Chicago to Rakovski | 5,273.02 mi (8,486.10 km) |
| Chicago to Razgrad | 5,267.14 mi (8,476.65 km) |
| Chicago to Razlog | 5,237.93 mi (8,429.63 km) |
| Chicago to Ruse | 5,233.14 mi (8,421.93 km) |
| Chicago to Samokov | 5,219.33 mi (8,399.70 km) |
| Chicago to Sandanski | 5,246.29 mi (8,443.09 km) |
| Chicago to Sevlievo | 5,242.36 mi (8,436.76 km) |
| Chicago to Shumen | 5,294.11 mi (8,520.04 km) |
| Chicago to Silistra | 5,264.11 mi (8,471.77 km) |
| Chicago to Sliven | 5,302.65 mi (8,533.79 km) |
