Chicago already let Walmart into the city years ago, even if the majority of their locations are focused primarily on groceries rather than full sized stores; Target's presence increases every year, especially when it comes to their smaller neighborhood focused stores; Walgreens has covered the Loop with so many locations that you can quite literally stand in one and see another; and Amazon rolled out its same day delivery and pickup service awhile ago, so no, I don't think this would work in Chicago. We crossed the Rubicon awhile ago.
That being said, some of them have been able to take advantage of historic buildings. Here's the Target on State St in the Loop:
https://www.google.com/maps/place/Ta...275442!6m1!1e1
Walgreens in Wicker Park:
https://www.google.com/maps/place/Wa...677768!6m1!1e1