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A novel chiral monomer end-capped with a cholesteryl group and threaded with β-cyclodextrin was synthesized in order to induce the formation of a helical polymer. 1H NMR studies revealed that one or two cyclodextrin molecules were threaded onto the synthesized chiral monomer, leading to the formation of a helical construction of self-assembled inclusion complexes. The formation of a self-assembled inclusion complex was identified using SEM and TEM. The monomeric self-assembled inclusion complex was further polymerized using benzoyl peroxide as a photoinitiator. Both the highly ordered alignment and the helical structure of self-assembled supramolecules were confirmed using polarized optical microscopy and circular dichroism spectroscopy, respectively. We have first demonstrated an easy process for the fabrication of helical polymers via self-assembled monomers threaded with a β-cyclodextrin end and capped with a chiral moiety.