In contextual optimization, the decision-maker seeks optimal decisions to minimize a cost function, that varies based on observed features. This context is common in many business applications ranging from on-demand delivery and retail operations to portfolio optimization and inventory management. In this paper, we study the learning and optimization approach, which first learns how outcomes result from the features, and then selects optimal decisions based on these outcomes. We focus on the integrated learning and optimization literature, and identify that a lack of control for prediction accuracy can lead to overfitting and a loss of decision effectiveness against simple separate learning and optimization models. Instead, we propose a bi-objective formulation that balances prediction accuracy and cost minimization, termed decision-driven regularization. It also addresses ambiguity in the definition of the cost function via a surrogate that depends on a new hyperparameter. We additionally show that alternative perspectives for formulating the problem, namely robust optimization and regret minimization, lead to models that are closely related to our proposed model. As a consequence, our framework generalizes models such as SPO+. Our model is shown to be numerically superior to other benchmarks, such as OLS, Random Forest, XGBoost, SPO+, Perturbation Gradient, and Learning and Rank, in our synthetic studies.

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