Regular health checkups are crucial for the identification of problems in connection with acute and chronic diseases. Early detection helps patients prevent disease progression, receive more effective treatment, and improve their overall prognosis and quality of life. In this context, the introduction of cost‐effective, advanced sensor technology for the monitoring of healthcare is an essential and unavoidable approach. The present study proposes a disposable triboelectric nanogenerator (TENG) based sensor for a novel urination condition evaluation methodology that is integrated with an artificial intelligence (AI) algorithm. The disposable TENG sensor is fabricated using chitosan‐covalent organic framework (CS‐NSCoF). The optimized CS‐NSCoF (4%) composite, in contact with fluorinated ethylene propylene (FEP), yields remarkable output performance metrics: a peak‐to‐peak voltage of 132 V, a short‐circuit current of ≈2.38 µA, and an average power density of 10.89 mW m−2 at a load resistance of 200 MΩ. Notably, biocompatibility assessments confirm the non‐toxic nature of the CS‐NSCoF sample in this investigation.