Trump likes Chicago because it fits his world view. Chicago is a city of two halves one poor and the other wealthy. As the wealthy do not have to endure, the City’s corrupt politics, it never changes. In a city where you have to pay to play, Trump would be at home. It fits his temperament. The public have to endure the cronyism, ghost work crews, rigged electoral registrations, and the failing public services like schools. Trump never has to worry about that experience because his wealth insulates him.
Chicago’s corruption does not serve the common good.
Chicago has been a corrupt and racist one party city for decades. In the past, it might have been excused for it still served a common good. Today, the city’s failures are an embarrassment to the nation. It is the most segregated city in the the country. Tt contains the brutal divide between rich and poor, whites and minorities, strong and weak. Chicago is Trump’s kind of town. In Chicago you are either a winner (rich, Trump) or a loser (poor and a minority). Chicago is two cities an Oligarchic city where you get justice, prosperity, opportunity and law and order; and the people’s city, where you get crime, poverty, and misfortune. In Chicago, the common good is an illusion.
Chicago has some of the wealthiest people in America and the world. Chicago’s elite are served by the city as it is presented as an Oligarch’s playground. Trump would be part of that establishment for that is how he behaves in New York. The wealthy benefit from the system and the system benefits them.
Chicago’s disappeared never get justice for no one speaks for them.
Trump claims he wants to help the less fortunate in Chicago. He promises to empower the police to deal with crime. The problem is that the police have the power and still fail to deal with crimes. Over the past few years, murder victims have disappeared from official statistics. In the city’s efforts to reduce the murder rate homicides have been changed to noncriminal deaths. Despite claims that better policing reduced the murder rate, the reality was the city massaged the figures. In Chicago, the disappeared are the weak, the vulnerable, and the voiceless. Those like Trump, the wealthy, powerful, and protected, get justice.
Police Shootings: If you are black the city is more likely to kill you or abuse you.
In Chicago, blacks, more than any other ethnic group, are more likely to be shot by the police. Laquan McDonald was the latest in a long line of people shot to death by Chicago police. Over the past 10 years, Chicago has paid out over half a billion dollars in compensation for these events. Such money could have helped to reduce crime, regenerate impoverished neighbourhoods, and improve schools. Despite these deaths and their cost, the Chicago Police act with near impunity with few officers disciplined or dismissed as a result. Trump would give them more power and less accountability. It is how he views the world.
Chicago is Trump’s kind of town.
 The Pritzkers symbolizes Chicago’s oligarchy which contains many other Chicago plutocrats. The Pritzkers are the highest profile. https://en.wikipedia.org/wiki/Pritzker_family http://www.chicagobusiness.com/article/20120307/NEWS01/120309839/chicago-has-18-of-worlds-richest-people-on-forbes-list Although they are not omnipotent http://evanstonnow.com/story/real-estate/bill-smith/2013-11-19/59640/alderman-kills-pritzker-bb-bid-in-chicago
 Between 2004 and 2014, the city paid out over $520 million in settlements, legal fees and other costs related to police misconduct, according to the Better Government Association.” http://data.huffingtonpost.com/2015/12/chicago-officer-misconduct-allegations
 http://www.truth-out.org/news/item/26986-amid-shootings-chicago-police-department-upholds-culture-of-impunity See also “Since 2001, civilians have lodged 20 complaints against Van Dyke. The complaints were not sustained by investigators. While it may seem surprising that so many complaints against one officer would be tossed out, a Huffington Post analysis of four years of city data released by the Invisible Institute, a non-profit journalism organization, reveals that there are more than 180 city police officers with more complaints than Van Dyke who weren’t disciplined at all over that time.” http://data.huffingtonpost.com/2015/12/chicago-officer-misconduct-allegations
 A person might say “Well, a Pritzker is never going to be shot by the police as they do not disobey police orders and they obey the law.” In this they would be correct. Yet, that misses the point. Would the police even dare to approach them with the same aggressiveness and brutality that they show to those in Lawndale or Austin? A critic would say “Well, they would not need to act aggressively as the situation could be resolved in a low key way; they are only a low level threat”. In this they would be true, but then we would remember that Laquan McDonald was not a threat.