The main result of this work is a homogenization theorem via variational convergence for elastic materials with stiff checkerboard-type heterogeneities under the assumptions of physical growth and non-self-interpenetration. While the obtained energy estimates are rather standard, determining the effective deformation behavior, or in other words, characterizing the weak Sobolev limits of deformation maps whose gradients are locally close to rotations on the stiff components, is the challenging part. To this end, we establish an asymptotic rigidity result, showing that, under suitable scaling assumptions, the attainable macroscopic deformations are affine conformal contractions. This identifies the composite as a mechanical metamaterial with a negative Poisson's ratio. Our proof strategy is to tackle first an idealized model with full rigidity on the stiff tiles to acquire insight into the mechanics of the model and then transfer the findings and methodology to the model with diverging elastic constants. The latter requires, in particular, a new quantitative geometric rigidity estimate for non-connected squares touching each other at their vertices and a tailored Poincaré type inequality for checkerboard structures.