We examine a recent prediction for the chirality dependence of the Casimir force in chiral metamaterials by numerical computation of the forces between the exact microstructures, rather than homogeneous approximations. Although repulsion in the metamaterial regime is rigorously impossible, it is unknown whether a reduction in the attractive force can be achieved through suitable material engineering. We compute the exact force for a chiral bent-cross pattern, as well as forces for an idealized “omega”-particle medium in the dilute approximation and identify the effects of structural inhomogeneity (i.e., proximity forces and anisotropy). We find that these microstructure effects dominate the force for separations where chirality was predicte...