There was an interesting article in the Tribune today about locals' pronunciation of Chicago. I suppose I have to admit that I say "Chi-CAW-go." The author of the article, Casey Bukro, calls those who say "Chi-caaaa-go" linguistic carpetbaggers.
He/she (?) has some other complaints as well, such as the frequent use of "environment." I hadn't noticed, but I see the point. Similarly, the author dislikes "if you will," and I have to agree. It always seems so contrived.