The densities, ρ, speeds of sound, u, and excess heat capacities, C P E data of binary mixtures formed by o-chlorotoluene with 1,3-dioxolane or 1,4-dioxane or tetrahydropyran at (298.15, 303.15, and 308.15) K and excess molar enthalpies, H E , of the same mixtures at 308.15 K have been measured over the entire composition range at atmospheric pressure. The excess molar volumes, V E , and excess molar isentropic compressibilities, κ S E , data have been calculated from experimental densities and speeds of sound data. The V E , κ S E , and H E values for o-chlorotoluene (1) + 1,3-dioxolane or 1,4-dioxane (2) mixtures are positive, and those for o-chlorotoluene (1) + tetrahydropyran (2) mixture are negative over whole range of composition. However, C P E values for the studied mixtures are positive over the entire range of composition. The V E , κ S E , H E , and C P E data have been estimated in terms of graph and Prigogine−Flory−Patterson (except C P E data) theories. The results indicate that V E , κ S E , H E , and C P E values estimated via graph theory are in agreement with experimental values.