Windy Gap may refer to:
- Windy Gap (Antarctica), a pass on the Louis Philippe Plateau
- Windy Gap (Wyoming), a mountain pass in Wyoming
- Windy Gap (Fremont County, Wyoming), a mountain pass in Wyoming
- Windy Gap (Lincoln County, Wyoming), a mountain pass in Wyoming
- Windy Gap, a pass on D'Aguilar Peninsula, Hong Kong Island, Hong Kong; see List of gaps in Hong Kong
- Windy Gap Trail in the Angeles National Forest, California