Chicago has been an active city since it started to attract people for new opportunities in the 1830s. After the city experienced the Great Fire in 1871, the primary concern was to rebuild the city. The absence of fire-protective materials, fragile soil conditions, and the need for multistory commercial buildings with structural stability were serious challenges. Many prominent architects and engineers not only rose to them but also created the “Commercial Style”. Thus, the time witnessed the emergence of the Chicago School. This paper addresses the influence of Louis Henry Sullivan on the Chicago School of Architecture. Looking at the remarkable ideas in materials and construction techniques employed at the time, it is aimed to answer how a city is built on its dynamics on a different scale. It provides an in-depth analysis of the period’s problems related to building construction via literature review, drawings, and photographs. As the method of the study, tall building innovations were investigated using Sullivan’s five buildings which express the idea of contemporary high-rise buildings and technical solutions of the period. The study will contribute literature answering how these buildings’ designs responded to the theory behind the Chicago School of Architecture.