Objectives: This study aimed to examine the various risk factors influencing chewing discomfort among Korean workers using data from the 2024 Community Health Survey. Methods: The 2024 Community Health Survey was conducted using an electronic questionnaire from May 16 to July 31, 2024, and 81,734 workers aged 20–64 years were analyzed. Results:Compared to professional and administrative managerial occupations, workers in sales/service jobs, simple manual labor, and other occupations showed significantly higher levels of chewing discomfort (1.588 times, 2.222 times, and 1.621 times, respectively). Workers with poor subjective oral health reported 44.635 times higher levels of chewing discomfort than those with good oral health. Mental health showed significant effects on sleep quality, sleeping pill use, work interruptions due to sleep, stress, and depression. Chewing discomfort increased 1.635 times in workers with high stress, and 4.718 times in workers with severe depression. Conclusions: The complex relationships between workers’ physical health, oral health, mental health factors, and chewing discomfort were comprehensively analyzed. This study highlights the need for integrated multidimensional oral health policies and programs aimed at improving workers’ overall health and quality of life.