Force the South Side to succeed into its own incorporated area. Problem solved for Chicago proper.
I suggest encouraging formation of a secession movement, kinda like what California but in reverse. Have the good parts give independence to the problem neighborhoods, and incorporate them into a new city called "Obamatown".
(I worked in Chicago for 5 years and my daughter earned her MS there. But I think the city is so dysfunctional that it is pretty much hopeless. The only question is the slope of the decline. Since they have decided on one-party-rule, even the Obamatown solution is only a temporary one.)