Computer-aided design (CAD) tools are widely used in the urban planning process, giving planners the ability to generate urban contexts and many scenarios for future development. However, debate is ongoing regarding CAD tools’ effects on student learning and the reliability of the cluster of assumptions that usually come with them. This article aims to examine whether CityCAD can be an effective tool for achieving learning objectives related to critical thinking, problem solving, and creativity in the urban planning discipline. This research also examines whether the software influences student interest in planning and affects student perceptions of the discipline. Using instructor observations, student projects, and surveys, we find that using CityCAD in education can achieve learning objectives, increase student interest, and enhance the perception of planning as a more creative field. The results have implications for instruction, student recruitment, and perceptions of the field.