The susceptibility of tools in Computer Numerical Control (CNC) machines makes them the most vulnerable elements in milling processes. The final product quality and the operations safety are directly influenced by the wear condition. To address this issue, the present paper introduces a hybrid approach incorporating feature extraction and optimized machine learning algorithms for tool wear prediction. The approach involves extracting a set of features from time-series signals obtained during the milling processes. These features allow the capture of valuable characteristics relating to the dynamic signal behavior. Subsequently, a feature selection process is proposed, employing Relief and intersection feature ranks. This step automatically identifies and selects the most pertinent features. Finally, an optimized support vector machine for regression (OSVR) is employed to predict the evolution of wear in machining tool cuts. The proposed method’s effectiveness is validated from three milling tool wear experiments. This validation includes comparative results with the Linear Regression (LR), Convolutional Neural Network (CNN), CNN-ResNet50, and Support Vector Regression (SVR) methods.