Background: Surgical resection remains the standard treatment for early-stage lung cancer. However, the recurrence rate after surgery is unacceptably high, ranging from 30% to 50%. Despite extensive efforts, accurately predicting the likelihood and timing of recurrence remains a significant challenge. This study aims to predict postoperative recurrence by identifying novel image biomarkers from preoperative chest CT scans. Methods: A cohort of 309 patients was selected from 512 non-small-cell lung cancer patients who underwent lung resection. Cox proportional hazards regression analysis was employed to identify risk factors associated with recurrence and was compared with machine learning (ML) methods for predictive performance. The goal is to improve the ability to predict the risk and time of recurrence in seemingly “cured” patients, enabling personalized surveillance strategies to minimize lung cancer recurrence. Results: The Cox hazards analyses identified surgical procedure, TNM staging, lymph node involvement, body composition, and tumor characteristics as significant determinants of recurrence risk, both for local/regional and distant recurrence, as well as recurrence-free survival (RFS) and overall survival (OS) (p < 0.05). ML models and Cox models exhibited comparable predictive performance, with an area under the receiver operative characteristic (ROC) curve (AUC) ranging from 0.75 to 0.77. Conclusions: These promising findings demonstrate the feasibility of predicting postoperative lung cancer recurrence and survival time using preoperative chest CT scans. However, further validation using larger, multisite cohort is necessary to ensure robustness and facilitate integration into clinical practice for improved cancer management.