The synthesis and optical properties of a variety of chiral polyolefins are reviewed. The polymers are separated into four categories: hydrocarbon‐based chiral polyolefins, chiral polyolefins from achiral monomers, chiral polyolefins with aromatic side chains, and chiral polyolefins bearing branched amino acids. The polymers were synthesized using Ziegler–Natta, anionic, radical, and acyclic diene metathesis (ADMET) polymerization techniques.