A Decision Support System (DSS) is proposed in this paper for improving container stacking operations. This DSS addresses the stacking problem for import containers via a two-step strategy. First, dwell times are predicted for each container using analytics techniques. This prediction is used as an input for a mathematical programming model that minimizes container rehandles heuristically. Numerical examples are presented using data from the Port of Arica in Chile as a case study. The results confirm the virtues of the proposed DSS to effectively support planning decisions at the container yard. Furthermore, results also show good performance of the operations at the yard in terms of rehandles in comparison with the current practices of this port terminal and well-known stacking strategies.