The main aim of this research work is to build a new practical hybrid regression model to predict the milling tool wear in a regular cut as well as entry cut and exit cut of a milling tool. The model was based on Particle Swarm Optimization (PSO) in combination with support vector machines (SVMs). This optimization mechanism involved kernel parameter setting in the SVM training procedure, which significantly influences the regression accuracy. Bearing this in mind, a PSO–SVM–based model, which is based on the statistical learning theory, was successfully used here to predict the milling tool flank wear (output variable) as a function of the following input variables: the time duration of experiment, depth of cut, feed, type of material, etc. To accomplish the objective of this study, the experimental dataset represents experiments from runs on a milling machine under various operating conditions. In this way, data sampled by three different types of sensors (acoustic emission sensor, vibration sensor and current sensor) were acquired at several positions. A second aim is to determine the factors with the greatest bearing on the milling tool flank wear with a view to proposing milling machine’s improvements. Firstly, this hybrid PSO–SVM–based regression model captures the main perception of statistical learning theory in order to obtain a good prediction of the dependence among the flank wear (output variable) and input variables (time, depth of cut, feed, etc.). Indeed, regression with optimal hyperparameters was performed and a determination coefficient of 0.95 was obtained. The agreement of this model with experimental data confirmed its good performance. Secondly, the main advantages of this PSO–SVM–based model are its capacity to produce a simple, easy–to–interpret model, its ability to estimate the contributions of the input variables, and its computational efficiency. Finally, the main conclusions of this study are exposed.