Which city is deader for the GOP: Chicago or San Francisco

[All Along The Watchtower]

I agree with virtually everyone when they say San Fran. Chicago (the city) is reflexively Democratic and San Fran is reflexively liberal... so as long as the Dems are the liberal party... then, yeah. But, yes, the issue is the suburbs. The San Fran suburbs are filled with wealthy, educated liberals... the Chicago suburbs are very middle-working class, white ... and prone to swing to the GOP.

The elitism your party manufactures about who its voters are is truly amusing.  The wealthiest people in Chicagoland are the ones who make the suburbs "GOP-friendly," SOMEWHAT offsetting the legions of poor people who make the city unwinnable.

If by "legions of poor people" you mean black and Latino voters (not all of whom are poor, FTR) , educated urban white liberals, as well as (to a lesser extent) working-class "ethnic" whites and pretty much everybody else in Chicago proper, than you have a point.

[All Along The Watchtower]

Wealthy white well-educated urban folks tend to vote Democratic;

^^But not nearly to the extent that urban working-class (especially non-white) voters are Democratic.
 
Also, a lot of well-educated Americans (particularly in large metropolitan areas-i.e. those very friendly to the Democrats- where there is a lot of competition for higher-paying jobs/the kind of jobs that require a Bachelor's Degree or higher) are not wealthy. Many (particularly but not exclusively the younger ones) work in service-sector type jobs that they are overqualified for (in terms of educational attainment, at least). Those urban residents who are younger, highly educated, less economically secure, and more transient than most other groups would vote very heavily for the Democrats, I suspect-to the extent that they vote at all, of course.