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In the wiki article and in the tribute article linked (https://www.chicagotribune.com/news/ct-xpm-1996-11-15-961115...), it doesn't really give any insight on why it was a 'disaster'. Have anymore to share? I'm really interested.

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It seems like this is an unsubstantiated claim. At the time that this change was introduced, Chicago was at the tail end of one of the longest economic declines that it has ever experienced. Several huge retailers that were located in the area closed around the same time. The hope was that changing this street into a pedestrian mall would save it from economic collapse. Unsurprisingly, it did not as the forces at work were much larger than anything that could be fixed by changing the traffic pattern on a single street.

https://chi.streetsblog.org/2013/03/11/why-was-the-state-str...

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