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I believe that political stripes really ought to be divided into 4 major groups to get a more accurate reading: Conservative (fiscally and socially conservative), Liberal (fiscally and socially liberal), Libertarian (fiscally conservative and socially liberal), and Populist (fiscally liberal and socially conservative). This is to reflect that there are large differences within the two major parties, which is particularly true in the Chicago area. For instance, even though the city of Chicago is almost completely Democratic territory, much of the South Side is largely made up of Populist blue collar union workers that are concerned with workers' rights but could care less about abortion rights while the North Side has white collar professionals that seem to be either on the Liberal or Libertarian side.
Here's my very general view of the political climate in the Chicago area - there are certainly exceptions within each area (personal disclosure - I consider myself to be a libertarian Republican, live in Naperville, grew up in the south suburbs, and have lived previously in the north suburbs, the north side of the city, and the south side of the city):
(1) North Side of the City, North Shore Suburbs, and West Cook County Suburbs: Liberals are the slight majority with Libertarians close behind them. Very few Conservatives and Populists.
(2) South Side of the City, West Side of the City, and South Cook County Suburbs: Mostly Populists and a sizeable number of Liberals. Very few Conservatives and Libertarians.
(3) DuPage County and Northwest Cook County Suburbs: Conservatives are the slight majority with Libertarians close behind them. The changes in the political climate here are similar to what has been happening in Orange County, California, where the trend is that the area is becoming more liberal on social issues, meaning that it's not nearly the solid Conservative base that it used to be. Very few Liberals and Populists.
(4) Lake County: Mostly Conservatives and Libertarians with a decent number of Liberals. As with DuPage County, the trend of the county is going more to the left on social issues. Very few Populists.
(5) Southwest Cook County Suburbs, Will County, Kane County, and McHenry County: Majority Conservative with a sizeable number of Populists. Very few Libertarians and Liberals. These fast-growing exurbs are becoming more of a reliable base for the Republican Party in Illinois than the suburbs located closer to the city.
Once again, these are just very general overviews. I know that there are certain exceptions to these generalizations, but these are just my overall impressions.
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