Now, more than ever, the planning and management of transportation systems in the real world is beset by change and uncertainty. Under these conditions, the quality of transportation education continues to be a matter of concern for the profession because of continuing demands and commitments at several levels. From an academic standpoint, topics such as public involvement, strategic management of capital resources, soft systems methodology, and applied ethics need to be incorporated in the curriculum in more substantial ways. On the basis of the demands of professional practice, as suggested by hiring agencies, the political working of the real world also needs to be understood by entry-level graduates. These and other relevant issues, relevant particularly for a graduate-level course on urban transportation planning, are described and discussed. On the basis of the “Millennium State-of-the-Art and Future Directions White Paper” sponsored by the Committee on Transportation Education, students are expected to have a deeper knowledge and acquire greater skills in the following four topics: intermodalism and systemicity, soft systems methodologies, applied ethics, and communication. A sample course outline incorporating these suggestions based on a three-credit course offered at the Illinois Institute of Technology, Chicago, in 2001 is described. Finally, the composition of the class and the student course evaluation are discussed. Overall, the course was well received by students.