An increase in unplanned downtime of machines disrupts and degrades the industrial business, which results in substantial credibility damage and monetary loss. The cutting tool is a critical asset of the milling machine; the failure of the cutting tool causes a loss in industrial productivity due to unplanned downtime. In such cases, a proper predictive maintenance strategy by real-time health monitoring of cutting tools becomes essential. Accurately predicting the useful life of equipment plays a vital role in the predictive maintenance arena of industry 4.0. Many active research efforts have been done to estimate tool life in varied directions. However, the consolidated study of the implemented techniques and future pathways is still missing. So, the purpose of this paper is to provide a systematic and comprehensive literature survey on the data-driven approach of Remaining Useful Life (RUL) estimation of cutting tools during the milling process. The authors have summarized different monitoring techniques, feature extraction methods, decision-making models, and available sensors currently used in the data-driven model. The authors have also presented publicly available datasets related to milling under various operating conditions to compare the accuracy of the prediction model for tool wear estimation. Finally, the article concluded with the challenges, limitations, recent advancements in RUL prognostics techniques using Artificial Intelligence (AI), and future research scope to explore more in this area.