The multiband, multifunctional chiral metasurface with asymmetric transmission exhibits significant potential for diverse applications in modern communication systems, ranging from enhanced signal modulation and polarization control to advanced beam steering and compact antenna design. This research presents a versatile and advanced chiral metasurface operating at multiple bands with diverse functionalities, including asymmetric transmission. The proposed metasurface effectively transforms an incoming Linearly Polarized (LP) wave into a Circularly Polarized (CP) wave. Additionally, it functions as a 90° polarization rotator for the incident LP wave. The design starts with an element of a 2 × 2 supercell comprising a Square Split Ring Resonator (SSRR) and an I-shaped resonator. The right diagonal elements of a supercell undergo scaling down, giving rise to a rotational asymmetry. Chirality is introduced into the design, and cross polarization conversion is enhanced by rotating all four elements by 90° relative to each other. On the back side of the substrate, each element undergoes a 90° rotation compared to its counterpart on the front side, realizing the asymmetric transmission feature. The incorporation of multiband and multifunctional features within a single supercell equips the subject chiral metasurface to be utilized in various engineering applications.