This paper is divided into five sections in addition to a conclusion. These five sections are: What was the Progressive Era? What was America like at the dawn of the Progressive Era? Were there early Predecessors of the Progressive Era? The Two Great Progressive Presidents and Chicago's Place in the Progressive Era. I define the Progressive Era as the time period in US history between roughly 1820 and 1920. I give a detailed explanation of the effect of the industrial revolution in America that resulted in a transitions from an agrarian economy to a manufacturing based economy. I then discuss the two US Presidents who passed the important progressive legislation during this time period, Theodore Roosevelt and Woodrow Wilson. In the Chicago section, I focus primarily on the founding of their neighborhoods and city. I conclude my paper with a comparison between the first Gilded Age (1870s to 1900) and the second Gilded Age (2000-2016) and discussion of why another Progressive Era may emerge. I found most of the facts cited on various Wikipedia website, which have been listed as footnotes.