This study aimed to determine the willingness-to-pay (WTP) values for dental checkups and analyze the association between the values and individual characteristics. This cross-sectional study was conducted using a nationwide web-based survey, and 3336 participants were allocated into groups that received regular dental checkups (RDC; n = 1785) and those who did not (non-RDC; n = 1551). There was a statistically significant difference in the WTP value for dental checkups between the RDC (median: 3000 yen [22.51 USD]) and non-RDC groups (2000 yen [15.01 USD]). In the RDC group, age 50–59 years, household income <2 million yen, homemaker and part-time worker employment status, and having children were significantly associated with decreased WTP values; male sex, household incomes ≥8 million yen, and tooth brushing ≥3 times daily were associated with increased WTP values. In the non-RDC group, age ≥30 years, household incomes <4 million yen, and having ≥28 teeth were significantly associated with decreased WTP values; household income ≥8 million yen was associated with increased WTP values. Conclusively, WTP values for dental checkups were lower in the non-RDC group than in the RDC group; in the non-RDC group, those with lower household income aged ≥30 years were more likely to propose lower WTP values, suggesting the need for policy intervention to improve access to RDC.