A computer-simulated reality and the human-machine interactions facilitated by computer technology and wearable computers may be used as an educational methodology that transforms the way students deal with information. This turns the learning process into a more participative and active process, which fits both the practical part of subjects and the learner’s profile, as students nowadays are more technology-savvy and familiar with current technological advances. This methodology is being used in architectural and urbanism degrees to support the design process and to help students visualize design alternatives in the context of existing environments. This paper proposes the use of virtual reality (VR) as a resource in the teaching of courses that focus on the design of urban spaces. A group of users—composed of architecture students and professionals related to the architecture field—participated in an immersing VR experience and had the opportunity to interact with the space that was being redesigned. Later, a quantitative tool was used in order to evaluate the effectiveness of virtual systems in the design of urban environments. The survey was designed using as a reference the competences required in the urbanism courses; this allowed the authors to identify positive and negative aspects in an objective way. The results prove that VR helps to expand digital abilities in complex representation and helps users in the evaluation and decision-making processes involved in the design of urban spaces.