Jumping crystals of racemic mixtures of asparagine monohydrate have been presented in this contribution to emphasize the key role of molecular chirality in governing the direction of macroscopic motions. When heated at the specific faces of the single crystals, a pair of enantiomorphs jump in opposite directions, which are further utilized for chiral resolution. The hydrogen-bonded networks between asparagine molecules in a specific direction provide oriented channels for the escape of water molecules during the dehydration, serving as a foundation for the directional crystal jumping. Our findings not only lay the foundation for the future creation of directed actuation systems based on dynamic crystals but shall also guide the efforts to reveal the correlation between chirality and motion across diverse realms of knowledge.