Filler–rubber composites were prepared by mixing chloroacetated natural rubber (CNR) with silica, carbon black (CB), or calcium carbonate using a two‐roll mill. The interactions between the CNR and fillers, including silica, carbon black, and calcium carbonate, were characterized based on glass transition temperature (Tg) and shear storage modulus (G′). The results showed that both the Tg and G′ values of the CNR‐Si composite were found to be higher than those of the CNR–CB and CNR–CaCO3 composites, indicating the existence of the CNR and silica interaction. The outstanding direct interaction between the CNR rubber matrix and silica without using a coupling agent was believed to be due to hydrogen bonds that formed between the hydroxyls of the silanol groups of silica and the carbonyls in the chloroacetate groups of CNR molecules. Moreover, it was also found that silica dispersed and distributed in the CNR matrix much better than in the natural rubber matrix. © 2015 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2016, 133, 43076.