Land-use intensification on arable land is expanding and posing a threat to biodiversity and ecosystem services worldwide. We develop methods to link funding for avian breeding habitat conservation and management at landscape scales to equilibrium abundance of a migratory species at the continental scale. We apply this novel approach to a harvested bird valued by birders and hunters in North America, the northern pintail duck (Anas acuta), a species well below its population goal. Based on empirical observations from 2007–2016, habitat conservation investments for waterfowl cost $313 M and affected less than 2% of the pintail’s primary breeding area in the Prairie Pothole Region of Canada. Realistic scenarios for harvest and habitat conservation costing an estimated $588 M (2016 USD) led to predicted pintail population sizes less than 3 M when assuming average parameter values. Accounting for parameter uncertainty, converting 70–100% of these croplands to idle grassland (cost: $35.7B–50B) is required to achieve the continental population goal of 4 M individuals under the current harvest policy. Using our work as a starting point, we propose continued development of modeling approaches that link conservation funding, habitat delivery, and population response to better integrate conservation efforts and harvest management of economically important migratory species.