Urban floodplain development brings economic benefits and enhanced flood risks. Rapidly growing cities must often balance the economic benefits and increased risks of floodplain settlement. Planning can provide multiple flood mitigation and environmental benefits by combining traditional structural measures such as levees, increasingly popular landscape and design features (green infrastructure), and non-structural measures such as zoning. Flexibility in both structural and non-structural options, including zoning procedures, can reduce flood risks. This paper presents a linear programming formulation to assess cost-effective urban floodplain development decisions that consider benefits and costs of development along with expected flood damages. It uses a probabilistic approach to identify combinations of land-use allocations (residential and commercial development, flood channels, distributed runoff management) and zoning regulations (development zones in channel) to maximize benefits. The model is applied to a floodplain planning analysis for an urbanizing region in the Baja Sur peninsula of Mexico. The analysis demonstrates how (1) economic benefits drive floodplain development, (2) flexible zoning can improve economic returns, and (3) cities can use landscapes, enhanced by technology and design, to manage floods. The framework can incorporate additional green infrastructure benefits, and bridges typical disciplinary gaps for planning and engineering.