As far as I know, Apple doesn't allow variations in the pricing of their products among retailers, so there should be no difference in price between NYC and Chicago except (same as the clothing) sales tax, with Chicago's being higher by ~1.3%. Depending on the version you're buying that's up to $5 more expensive in Chicago. ie not much difference. In Chicago, if you're still going to be near Michigan Ave, there is an Apple Store on Michigan or a Best Buy in the Hancock building depending on where you stay or are shopping.