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Conventional free radical polymerization of (hydroxy)alkyl-containing vinylimidazolium ionic liquid monomers generated high molecular weight polymers. A study of these materials was undertaken to relate chemical composition to macromolecular properties. Varying the substituent chain length and functionality of these polymerized ionic liquids (PILs) significantly influenced numerous polymer properties. Incorporation of a hydroxyl group at the terminus of the alkyl substituent lowered the glass transition temperature (T_g) of the PILs ∼50 °C and increased homopolymer thermal stability compared to the respective alkyl analogue. X-ray scattering demonstrated that (hydroxy)alkyl chain length influenced polymer backbone-to-backbone spacing. More importantly, X-ray scattering showed hydroxyl incorporation diminished the local compositional heterogeneity present in the alkyl-functionalized vinylimidazolium …