Modulating biological functions often relies on structural changes mediated by molecular switches. However, conventional achiral molecular switches designed to mimic biological regulation intrinsically fail to capture chirality-dependent processes. To address this limitation, engineered chiral molecular switches offer a promising strategy for elucidating the role of chirality in living organisms. Herein, we report a family of pH-sensitive, chromenoindole-based chiral switches ( CI-1 to CI-6) that exhibit distinct multicolor chromism—from yellow to azure—upon acid-induced ring-opening, generating the corresponding zwitterionic species ( ZI-1 to ZI-6). These switching processes are fully reversible and can be triggered by the addition of base, leading to original colorless solutions. Chiral chromatographic separation afforded enantiomerically pure molecular switches. By combining theoretical calculations with experimental circular dichroism (CD) analysis, we assigned the absolute configurations of (5aR,10bR)/(5aS,10bS)-CI-3, CI-4, and CI-5. These chiral switches exhibited attenuated chiral signals upon ring opening due to the loss of one chiral center, with full signal restoration upon neutralization. This family of structurally simple yet functionally versatile chiral switches offers both mechanistic insights and practical potential for the development of smart materials.