Cylindrical grinding is commonly used as the final process of machining, but its quality and efficiency are often limited by chatter phenomenon. Many research show that the result from conventional chatter analysis by using the deterministic parameters is not consistent with the practical working condition and the chatter reliability prediction in high speed cylindrical grinding with uncertain parameters is studied in this paper. The dynamic model of the cylindrical grinding system is established, and uncertain parameters such as mass, stiffness and damping coefficient are introduced, and the stability lobe diagrams with uncertain parameters were obtained. The reliability model of the grinding system was established, and the reliability was solved by using the Monte Carlo simulation method, the improved first-order second-moment method and the second-order second-moment method, respectively. Then, the chatter-free reliability of the system was predicted by using the reliability lobe diagram. The accuracy of the grinding reliability prediction results is verified by the experiment results. Furthermore, the Monte Carlo sensitivity analysis method is used to study the influence of random parameters on the grinding system, and the results show that the variation of modal mass has the greatest influence on the reliability of the grinding system.