The only things I know about Chicago that are remotely "insidery" are things I parrot from the Chicago Reader's Ben Joravsky, Chicago's most important writer.
I just realized today that he does a weekly webcast where he does a brief Q&A about his newest weekly political feature. The nuts and bolts of it, is that he's the best informed, most consistent, and most forthright Mayor
Particularly important is his work about Chicago's Olympic bid (he's staunchly against it, out of distrust for Mayor Daley, not because he's a stick-in-the-mud), Chicago's parking meter leasing fiasco, and our less-than-awesome TIF/slush funds for Mayor Daley.
So if you sorta want to see what's going on in Chicago politics, but you don't feel like spending much time doing so, that podcast is a great place to start.
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