The polyaddition of isocyanate and polyol to form polyurethane elastomers has rarely been applied to the construction of chiral polyurethane elastomers. Hence, the introduction of chiral units via polyaddition remains a challenging subject in polymer chemistry. In this study, the synthesis of chiral polyurethane elastomers using an aromatic isocyanate, polyols (polyether and polyester polyols), and L(+)-, D(−)-, or meso-tartaric acid by a one-shot method is investigated. The polymers are characterized using FTIR and NMR spectroscopy, and their thermal properties are investigated by TGA, DMA, and DSC analyses. The optical activities of the polymers are confirmed by rotation. The use of chiral tartaric acids is essential to obtain the desired chiral polyurethane elastomers.