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<italic>Objective:</italic> Chronic diseases have become the most prevalent and costly health conditions in the healthcare industry, deteriorating the quality of life, adversely affecting the work productivity, and costing astounding medical resources. However, few studies have been conducted on the predictive analysis of multiple chronic conditions (MCC) based on the working population. <italic>Results:</italic> Seven machine learning algorithms are used to support the decision making of healthcare practitioner on the risk of MCC. The models were developed and validated using checkup data from 451,425 working population collected by the healthcare providers. Our result shows that all proposed models achieved satisfactory performance, with the AUC values ranging from 0.826 to 0.850. Among the seven predictive models, the gradient boosting tree model outperformed other models, achieving an AUC of 0.850. <italic>Conclusions:</italic> Our risk prediction model shows great promise in automating real-time diagnosis, supporting healthcare practitioners to target high-risk individuals efficiently, and helping healthcare practitioners tailor proactive strategies to prevent the onset or delay the progression of the chronic diseases.