We propose a class of chiral charge density waves (CDWs), dubbed winding CDWs, that exhibit macroscopic chirality despite a single ordering wavevector. In screw-symmetric chiral crystals, chiral phonons drive a Peierls instability that selects a definite crystal angular momentum channel, thereby endowing the CDW with an integer azimuthal phase winding dictated by the selection rule governing electron–phonon coupling. We further extend this framework to achiral crystals with discrete rotational symmetry and demonstrate that spontaneous symmetry breaking stabilizes a winding CDW with either handedness, realizing an achiral-to-chiral phase transition. Our results reveal a fundamental link between the geometry of chiral structures and the phase topology of electronic orders.