Every time we visit a city for fun or business, we take note of the sorts of iPods and iPhones we see—and don’t see—on the streets and subways, as well as the performance of our iPhones as we’re traveling around. We spent this weekend in downtown Chicago for the annual Taste of Chicago, and were frankly very surprised at what we found: a higher density of iPod classics/5Gs than anywhere we’ve seen before, with a considerable…