Objectives: This article examines the diversity of healthy cities evaluation in practice and discusses the major conflicting issues in evaluating healthy cities to offer implications to academics and cities for application in their field. Methods: The author discusses issues on major topics that arose from a review of literature on selected articles from peer-reviewed journals, books and gray literature. The recently developed Korean Healthy Cities evaluation framework is used as a main source of reference. Results: Evaluating healthy cities is in itself a political process and requires multiple methodologies and diverse sources of data. Details of the evaluation process depend on the purposes and goals predetermined by the stakeholders. The Korean Healthy Cities evaluation framework applies these principles and suggests a participatory approach to evaluation, selection of indicators that provide evidence on the process of change and to use mixed evaluation methods. The involvement of stakeholders in the evaluation process can also be a useful tool to further strengthen partnerships and strategies for healthy cities. Conclusion: Cities need to engage more in evaluation activities and develop necessary skills and capacity to produce utility-driven evidence.