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What economic and political effect it would have on both cities and nations? Do you think they would grow larger than they are today? Do you think they would jointly cooperate and operate airports? I assume roadways, rails, trains, subways would be maintained by each side of two countries separately with some common links like Chicago skyway by both. So what it would be if Chicago was where it is today and Toronto in Indiana.
Odd question.
Simply: it just wouldn't happen.
When both cities just starting out one would be come dominate and there would be no need for the other to grow that large. Unless there was some huge natural resource there to exploit,
There's a reason you don't see huge cities across the border from each other in many places. Maybe in Europe, but even that is kind of rare...
It would all stay the same just with easier access to both cities with skyways like you mentioned. There wouldn't be a common metropolitan area between the two cities because they are still in different countries so Toronto would still be GTA. Kinda like with Windsor and Detroit. Nothing would happen because they are in two different countries, except for maybe Toronto gaining more of an American culture with Chicago so close by.
Peregrine, I think you missed the point. The OP knows this would never happen realistically, but imagine for the sake of argument that Toronto and Chicago were situated in an almost NYC/New Jersey manner.
If that's the case, then I believe that each city would grow exponentially in size over time because they would because each countries respective international trading ports, international government relations buildings, as well as tourism. Remember this is now one of the largest super metropolitan areas on earth. The cities would compete with each other for tourism and each grow along with it. American youth would cross for Ontario's younger drinking age, and Canadian's would return for the cheaper shopping. Toronto would likely gain a few casino's in an almost Windsor/Detroit fashion.
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