Many biological materials such as tendons and muscles contain helical fibers. In this paper, the fracture behavior of such chiral composites is investigated through a combination of theoretical analysis and finite element simulations. A mesoscopic fracture mechanics model of helical fiber-reinforced biological composites is presented, with the effects of interfacial damage and fiber breakage. A cohesive law is adopted to characterize the interfacial damage induced by the relative slipping between the fibers and the matrix. The theoretical model agrees well with the numerical results. The optimized fiber radius that can maximize the fracture toughness of the composites is determined. The effects of interfacial (e.g., bonding strength and energy dissipation) and material properties (e.g., strength and elastic modulus) on the resistance to crack propagation are revealed. Our results show that the composites reinforced by helical fibers exhibit comprehensively excellent mechanical properties, e.g., simultaneous high strength, stiffness, and fracture toughness. This work not only helps understand the structure–property interrelations of biological chiral composites, but also provides inspirations for designing high-performance engineering materials.