The introduction of structured microsphere composites into hydrogels is found to improve their mechanical strength capability. Herein, chitosan microspheres were functionalized with poly(acrylamide-co-1-benzyl-3-vinylimidazolium bromide) (CS-P(AM-G)), which was synthesized through an in situ copolymerization of acrylamide and a guest functional monomer. Supramolecular hydrogels were fabricated by dynamic host-guest interactions between guest units and the host molecule cucurbit[8]uril (CB[8]). Investigations on the mechanical properties of the hydrogels show that the tensile stress and the compress stress of the hydrogels are five times higher than those of CB[8] hydrogels without CS, and the healing efficiency of the hydrogels at room temperature is 88% after 24 h. The results show that CS microspheres serve as both polyfunctional initiating and cross-linking centers, whereas the dynamic host-guest interactions endow the hydrogels with a higher self-healing property. The process provides a novel method for the production of tough and self-healing supramolecular hydrogels with various potential applications.