Technologies to harvest electrical energy from wind have vast potentials because wind is one of the cleanest and most sustainable energy sources that nature provides. Here we propose a flutter-driven triboelectric generator that uses contact electrification caused by the self-sustained oscillation of flags. We study the coupled interaction between a fluttering flexible flag and a rigid plate. In doing so, we find three distinct contact modes: single, double and chaotic. The flutter-driven triboelectric generator having small dimensions of 7.5 × 5 cm at wind speed of 15 ms(-1) exhibits high-electrical performances: an instantaneous output voltage of 200 V and a current of 60 μA with a high frequency of 158 Hz, giving an average power density of approximately 0.86 mW. The flutter-driven triboelectric generation is a promising technology to drive electric devices in the outdoor environments in a sustainable manner.