Data-enabled smart transportation has attracted a surge of interest from machine learning and data mining researchers nowadays due to the bloom of online ride-hailing industry and rapid development of autonomous driving. Large-scale high quality route data and trading data (spatiotemporal data) have been generated every day, which makes AI an urgent need and preferred solution for the decision making in intelligent transportation systems. While a large of amount of work have been dedicated to traditional transportation problems, they are far from satisfactory for the rising need. We propose a half-day workshop at CIKM 2019 for the professionals, researchers, and practitioners who are interested in mining and understanding big and heterogeneous data generated in transportation, and AI applications to improve the transportation system. We plan to have several invited talks from both academia and industry. This workshop would be organized by Shanghai Jiao Tong University, Didi Chuxing and Pennsylvania State University.