This book presents research in the way we analyze and design cities. Its purpose is to propose a multidisciplinary approach to urban design by combining quantitative and qualitative methods in order to create more robust and accurate end solution to complex urban problems. Through the use of simulation software mixed with urban design theory and phenomenology, the research in this book looks for a solution to specific urban problems existing in St. Louis, Missouri. This city in general has had significant decline in the past 60 years ever since the introduction of the interstate sliced through the urban fabric and has destroyed many vital connections that made the city work. With the understanding that spatial configurations are the critical components for physically determining how urban systems perform, we can analyze and resolve them and couple their solutions with vibrant urban spaces. By using this approach we can bring the thriving urban centers back to our cities.