That's a tall order Rob. I guess we can start things off with the western and southern limits of the city obviously defining two things for us. Would you agree that we can use the Sanitary & Ship Canal as the north boundary for the SW side? If one arbitrarily selects California Ave at 2800W then yes, you would be excluding Morgan Park and placing that into the South Side but raising another question. What would you consider the area east of California but say north of 79th St. for example? Maybe suggesting the use of streets is not the appropriate way of separating the areas of Chicago, but rather the boundaries are what any individual perceives them to be.
As a life long Channel 5 news viewer I'll offer further proof of the individual hypotheses concept. Oftentimes they have no clue as to the areas of Chicago!