That's interesting. I actually grew up in Chicago, but have most recently lived in Iowa. I don't have much of a "chicago" accent with the notable exception of saying "rough" and "roof" exactly the same way.
What got me, as an east coast transplant, was the use of "pop" versus "coke" or "soda." I literally wouldn't register it when people would ask me: "hey do you want a pop?" I'd be like, <pause> "wait, what about your father?" This is even though I knew they called it pop in the Midwest, and over a period of years. It would just catch me off guard.
