Having been born and raised there I beg to differ. Chicago has always been a political cesspool dating back to the old Ward 1 pols and the Haymarket riots. As a college student in the 50's I was taught 'economics' by openly Communist profs and asst. profs at the Univ. of Illinois. (Navy Pier branch at that time). The politics that made the city work were not so much free enterprise as pay to play, exactly what you see these days in DC. Even at the local Ward level if you wanted anything it was well known that you had to pay off one way or another. Now what you see is one corrupt political faction fighting with another corrupt faction for the dwindling supply of money due to the policies of the Marxist adventurer (from Chicago) now in the White Mosque. No, Chicago may have a pretty front yard but behind the facade is a pile of garbage that made the old stock yards smell like perfume.
Chicago in the Gilden Age was a mecca for businessmen, industrialists, with high advancements in architecture and construction. Im talking about 1870 to 1900.