This paper reports experimental excess molar volumes V_m^E using a digital vibrating-tube densimeter and excess molar enthalpies H_m^E by means of an isothermal microcalorimeter with a flow mixing cell for the binary mixtures {1,2-dichloropropane+1,3-dioxolane} and {1,2-dichloropropane+1,4-dioxane} at 298.15 K under atmospheric pressure. The mixture of {1,2-dichloropropane+1,3-dioxolane} has negative V_m^E over the entire composition range with exception of 1,4-dioxane, which has been shown to be positive. The cyclic molecular shape of 1,4-dioxane is not ideal to accept the halogenated hydrocarbon, resulting in an increase in the molecular distance. The consequent loosening of intermolecular intersections is also responsible for the positive values of V_m^E, with the exception of 1,3-dioxolane, due to its smaller molecular size. The excess enthalpies of all these mixtures were found to be positive over the entire composition range. These negative deviations from ideal behavior are probably due to dipole and dipole interaction between Cl and O molecules. The values of excess molar properties were fitted by the Redlich-Kister equation using Nelder-Mead’s simplex pattern search method.