Background: As dengue is a preventable vector-borne disease, the community's knowledge, attitude, and health-seeking behavior play an important role in successfully preventing the upsurge of cases and reducing mortality. This study thus tried to assess the knowledge, awareness, and health-seeking behavior among the Urban Kolkata residents. Methods: A cross-sectional observational study was performed among urban residents visiting the community healthcare center in Urban Kolkata. The survey questionnaire was formulated, tested, and administered to assess the knowledge, awareness, and health-seeking behavior regarding dengue. Responses were statistically analyzed. Results: The study was conducted on 158 residents of Urban Kolkata. 69.62% of individuals pointed out stagnant water as a prime mosquito breeding area and 77.22% of subjects held dark indoor places as the main resting place of dengue mosquitoes during the day. All respondents believed that cleaning mosquito breeding and resting places and using mosquito repellents were the most preventive measures. 83.54% of respondents believed cleaning the house surrounding to be an effective mode of breeding prevention. 51.90% of respondents would attend a government healthcare facility in the event of encountering fever, followed by 20.25% opting for private consultation and 18.99% self-treating themselves with over-the-counter drugs. Only 39.34% knew that bleeding was a warning sign. Knowledge parameters showed a significant positive association with age and educational status (p = 0.001). Conclusion: Dengue awareness is essential to prevent and control the spread of the disease, reduce its impact on public health, and foster a sense of responsibility within the community. Public health campaigns, educational programs, and community engagement are important tools in raising awareness about dengue and its prevention.