The Apparel Center, as catastrophically ugly as it is, is still in good structural shape, mostly fully leased and profitable. Unlikely its going away anytime soon, unless a big time corporate entity wants to build a trophy tower here.
The ECB on the other hand probably has a more realistic chance of getting redeveloped at some point. I could see them voluntarily moving if the price is right. Probably wont happen until all available lots in the immediate vicinity have already been developed, however. There's still tons of land north of Chicago Ave, although those come with costly affordable/subsidized housing strings attached that is keeping development at bay there for now as well.
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"Eventually, I think Chicago will be the most beautiful great city left in the world." -Frank Lloyd Wright
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