| Winnetka to Popovo | 5,254.63 mi (8,456.51 km) |
| Winnetka to Provadia | 5,304.83 mi (8,537.30 km) |
| Winnetka to Radnevo | 5,295.94 mi (8,522.99 km) |
| Winnetka to Radomir | 5,175.93 mi (8,329.85 km) |
| Winnetka to Rakitovo | 5,244.72 mi (8,440.56 km) |
| Winnetka to Rakovski | 5,261.80 mi (8,468.05 km) |
| Winnetka to Razgrad | 5,255.48 mi (8,457.87 km) |
| Winnetka to Razlog | 5,227.01 mi (8,412.06 km) |
| Winnetka to Ruse | 5,221.50 mi (8,403.19 km) |
| Winnetka to Samokov | 5,208.31 mi (8,381.96 km) |
| Winnetka to Sandanski | 5,235.46 mi (8,425.66 km) |
| Winnetka to Sevlievo | 5,230.98 mi (8,418.46 km) |
| Winnetka to Shumen | 5,282.43 mi (8,501.25 km) |
| Winnetka to Silistra | 5,252.24 mi (8,452.66 km) |
| Winnetka to Sliven | 5,291.17 mi (8,515.31 km) |
