In this paper, a hybrid machine learning model is applied to evaluate the relationship between random initial states and the power system’s vulnerability to cascading outages. A cascading outage simulator (CS), which uses off-line AC power flows, is proposed for generating training data. The initial states are randomly selected and the CS model is deployed for each initial state, where power system generation and loads are adjusted dynamically and power flows are redistributed to quantify the vulnerability metric. Furthermore, the proposed hybrid machine learning model deploys a combined Support Vector Machine (SVM) classification and Gradient Boosting Regression (GBR) to improve the learning precision. The classification model is trained by SVM, which divides the data into two categories with and without load shedding. Then, GBR is adopted only for the data with load shedding to determine the relationship between input power outage states and the vulnerability metric. The proposed vulnerability analysis approach is applied to several test systems and the results are analyzed. <italic xmlns:mml="http://www.w3.org/1998/Math/MathML" xmlns:xlink="http://www.w3.org/1999/xlink">Note to Practitioners</i> —The power system vulnerability can be quantified by cascading outage simulations. However, there are two challenges: i) there are a huge number of possible initial states and we cannot enumerate all these initial states for the cascading outage simulation. Neither can we precisely quantify the bus vulnerability. ii) The cascading outage simulation may be time-consuming for large-scale power systems, which is challenging for the online application. To address the above challenges, we expect to design a machine learning technique to predict the power system vulnerability, which can train the model in an offline way and then use it for the online application. Firstly, since there is not enough operation data from practical power systems, we develop a cascading outage simulator, using off-line AC power flows, for generating synthetic training data. Secondly, we observe that the training precision by directly applying the regression model may be very poor because the output of the machine learning model may take on an uneven distribution concerning input parameters. Thus, we propose a hybrid machine learning model with a combined classification and regression method, where the classification model is employed to remove the data without the load shedding, and the regression model then determines the relationship between input power outage states and the vulnerability metric. The proposed model and method have been tested on several systems including a practical large-scale Polish power system to show the effectiveness.