Helical ladder polymers are designed by connecting planar indenofluorene chromophores by chiral triptycene linkers. The resulting hexagonal helices exhibit a substantial degree of homoconjugation across the triptycene knots, with saturation above ≈20 repeat units. The chiroptical anisotropy values gabs = Δε/ε of the lower-energy lobes of the red-most couplets in the circular dichroism (CD) spectra arise from the π−π* transition of the planar indenofluorene chromophores and increase almost sevenfold when going from a model dimer to the corresponding polymeric helical ladder structures. This increase represents a signature of “chiral amplification” that is observed at the molecular, single-chain level. Here, the incorporated chiral linker units determine the chiroptical properties of the helical polymer chain, with chiral interactions arising across many achiral indenofluorene building blocks (>12). This behavior is observed for a fully covalently bound single polymer chain, in contrast to the more commonly studied supramolecular assemblies of appropriate chiral molecules.