Bridge expansion and contraction installation (BECI) has proved to be an essential component of the bridge structure due to its stability, comfort, and durability benefits. At present, traditional replacement technologies for modular type, comb plate type, and seamless type BECIs are widely applied worldwide. Nevertheless, it is unfortunate that the research conducted on decision-making (DM) approaches for the technical condition assessment and the optimal replacement plan selection of existing BECIs remain scarce, which results in the waste of resources and the increase in cost. Therefore, a BECI technical condition assessment approach, which contains specific on-site inspection regulations with both qualitative and quantitative descriptions, is proposed in this research, and a corresponding calculation program has been developed based on the MATLAB platform, which provides the basis for the necessity of replacement. Simultaneously, the hybrid chaotic whale optimization algorithm is designed and performed to improve and automate the process of optimal replacement plan selection under the assistance of the analytic hierarchy process (AHP), where both the achievement in consistency modification and the reservation of initial information are perused, and its superiority and effectiveness are verified via the comparative experimental analysis. The improved BECI replacement decision system is established, and the corresponding case study demonstrates that the proposed system in this research proves reasonable and feasible. The improved system can effectively assist bridge managers in making more informed operation and maintenance (O and M) decisions in actual engineering projects.