The chaotic proliferation of skyscrapers in many cities around the world is contributing to a decline in placemaking. This book examines the role of skyscrapers and open spaces in promoting placemaking in the city of Chicago. Chicago’s skyscrapers tell an epic story of transformative architectural design, innovative engineering solutions, and bold entrepreneurial spirit. The city’s public plazas and open spaces attract visitors, breathe life, and bring balance into the cityscape. Using locational data from social media platforms, including Twitter, Facebook, and Instagram, along with imagery from Google Earth, fieldwork, direct observations, in-depth surveys, and the combined insights from architectural and urban design literature, this study reveals the roles that socio-spatial clusters of skyscrapers, public spaces, architecture, and artwork play to enhance placemaking in Chicago. The study illustrates how Chicago, as the birthplace of skyscrapers, remains a leading city in tall building integration and innovation. Focusing on some of the finest urban places in America, including the Chicago River, the Magnificent Mile, and the Chicago Loop, the book offers meaningful architectural and urban design lessons that are transferable to emerging skyscraper cities around the globe.