Chemical recycling to monomers (CRMs) of A–B–A block copolymers is governed by the chemical structure and thereby the thermodynamic behavior of different block constituents. Here, we show how a thermodynamic toolkit based on a cyclic monomer structure and solvent properties can be utilized in the design of recyclable A–B–A block copolymers with varying material properties. By combining four cyclic monomers lactide, ε-decalactone, 2,2-diethyltrimethylene carbonate, and trimethylene carbonate, three different block copolymers were created, suitable for different CRM scenarios. The chemical structure of the soft midblock (ε-decalactone or trimethylene carbonate) appeared to have a critical impact both on the ring-closing depolymerization behavior and mechanical properties, where changing from a polyester to a polycarbonate soft block increased Young’s modulus from 14 to 200 MPa. Hence, this work demonstrates the complexity as well as the opportunities in the design of macromolecular structures for a circular economy.