A straightforward two-step synthesis protocol affords a series of chiral amide-based bis-pyridine substituted polyether macrocycles. One ligand is particularly able to complex terbium(III) ions spontaneously. Upon complexation, interesting chiroptical properties are observed both in absorbance (ECD) and in fluorescence (CPL). In ligand-centered electronic circular dichroism, a sign inversion coupled with a signal enhancement is measured; while an easily detectable metal-centered circularly polarized luminescence with a g_lum of 0.05 is obtained for the main ⁵D₄ → ⁷F₅ terbium transition. The coordination mode and structure of the complex was studied using different analysis methods (NMR analysis, spectrophotometric titration and solid-state elucidation).