Machining refers to a variety of processes, in which a cutting tool is used to remove the unwanted material from a workpiece. Tool wear, advertently or inadvertently, occurs after long-time use. It is crucial to monitor the tool wear so that the cutting tool can deliver the best performance and meet the technological challenges nowadays. In this paper, through different fractional-order chaotic systems, i.e., Chen-Lee, Lorenz, and Sprott, extension theory is proposed to predict the tool life. The results of the three chaotic systems are compared. The centroid of the 2-D plane of dynamic errors is used as the characteristics. Four wear states are defined in accordance with different levels of surface roughness, i.e., normal, slight, moderate, and severe. The boundaries of the four states are identified according to the locations of the centroid generated with the systems of different fraction orders. The boundaries are then fed into the extension model, and the relational function calculation is performed. In this way, the identification of tool state can be easily achieved. The experiment results indicate that Chen-Lee system and the Lorenz systems exhibit the same diagnosis rate (97.375%), higher than that of the Sprott system (35.75%). It is demonstrated that the two chaotic systems are fit for use with the method proposed in this paper. It is also proven that Chen-Lee and Lorenz fractional-order master-slave chaotic systems are very effective for tool life monitoring. The robustness of diagnosis is also greatly improved. INDEX TERMS Fractional order chaotic system, cutting, wear, machine tool.