In recent decades, polymer research has focused on developing self-healing materials that work efficiently without external stimuli for a broad range of applications. The introduction of hydrogen bonding units within such materials can promote their self-healing behavior with opportunities for its further refinement due the long-range arrangement of hydrogen bonds. Herein, we examine the impact of introducing 1,2-disubstituted cyclohexyl thioureas (TUCyH) into ethylene glycol polymers to understand the impact of chirality on their properties, in particular their self-healing. We find that their introduction leads to the controlled formation of rigid domains bearing a well-packed structure reinforced by hydrogen bonds that are critical for the material's mechanical robustness and stability and the zigzag arrangement of the polymer chains augments self-healing by sliding after damage. This structural design minimizes the risk of premature failure or degradation under stress, thus extending the durability of the material. Importantly, we show that the introduction of chiral domains such as in the co-polymer poly(TUEG3-90-TUCyH-10) can be a promising approach to engineer enhanced stability and sustained self-healing performance in supramolecular polymer materials.