U.S. teachers have less time to plan, collaborate, and research related work in comparison to teachers in competing countries (NECTL) and time is needed for teachers to learn new skills, understand new concepts, and to integrate new ideas into their practice (Corcoran, 1995). The MSUrbanSTEM Teaching and Leadership Fellowship program is a professional development program that works with a selected group of K-12 STEM teachers in the Chicago Public School system. This untraditional program tackles the issues of teachers needing more time to learn new skills and integrate them into practice by using one academic year to develop teachers in four ways: (a) Inspiring teachers to embrace an Deweyian educative experience to teaching, (b) encouraging an unorthodox approach and lens to teaching and learning, (c) creating supportive teaching communities, and (d) expanding teacher pedagogical practices with technology and creativity. These four theoretical frameworks make up the overall philosophy that grounds the UrbanSTEM program while always considering the challenges, benefits, and unique customs of urban context that the teachers work. This chapter also includes some reactions of some of the participating fellows, expressing what they learned from this program and how it inspired them or altered their view.