Out of curiosity, do you see Chicago expanding its city limits in your lifetime?
First off I want to say, I've never been but as an architecture and city lover, I hope to visit one of these days.
Seeing from videos your city seems to have lots of potential for very expansive growth.
I do think it's theoretically possible in very far off future for Chicago metro area to get close to LA metro's population. And I say this as an LA native. AKA the biggest suburb in America. See that I didn't say city.