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To be fair I haven't spent enough time in Chicago to give an opinion on it, but since I am originally from the Twin Cities I have to say the Bears suck (well maybe not right now). Some of my favorite cities have been New Orleans and San Francisco. Having just recently gone to Tokyo I would agree that it's in a top 20 list, but I enjoyed Kyoto more than Tokyo.
You, me, the yard behind the school, sir... Oh, wait... you said Bears? Yeah, da Bears still suck.