NASA envisions a future Air Traffic Management system that allows safe, efficient growth in global operations, enabled by increasing levels of automation and autonomy. In a safety-critical system, the introduction of increasing automation and autonomy has to be done in stages, making human-system integrated concepts critical in the foreseeable future. One example where this is relevant is for tools that generate more efficient flight routings or reroute advisories. If these routes are not operationally acceptable, they will be rejected by human operators, and the associated benefits will not be realized. Operational acceptance is therefore required to enable the increased efficiency and reduced workload benefits associated with these tools. In this paper, the authors develop a predictor of operational acceptability for reroute advisories. Such a capability has applications in tools that identify more efficient routings around weather and congestion and that better meet airline preferences. The capability is based on applying data mining techniques to flight plan amendment data reported by the Federal Aviation Administration and data on requested reroutes collected from a field trial of the NASA developed Dynamic Weather Routes tool, which advised efficient route changes to American Airlines dispatchers in 2014. 10-Fold cross validation was used for feature, model and parameter selection, while nested cross validation was used to validate the model. The model performed well in predicting controller acceptance or rejection of a route change as indicated by chosen performance metrics. Features identified as relevant to controller acceptance included the historical usage of the advised route, the location of the maneuver start point relative to the boundaries of the airspace sector containing the maneuver start (the maneuver start sector), the reroute deviation from the original flight plan, and the demand level in the maneuver start sector. A random forest with forty trees was the best performing of the five models evaluated in this paper.