Ion dynamics and charge transport in a homologous series of imidazolium chloroaluminate ionic liquids are investigated by broadband dielectric spectroscopy, rheology, viscometry, and differential scanning calorimetry. The interplay of anion speciation and alkyl chain length on local and mesoscale dynamics and the corresponding influence on the dc ionic conductivities, zero-shear viscosities, and static dielectric permittivities is investigated. These results are presented within a broader framework of current understanding of dynamics and transport properties of aprotic ionic liquids.