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Originally Posted by the urban politician
^ You seem to keep wanting to hammer this issue without acknowledging that Chicago tried a similar experiment on State St 35 years-ish ago (it was bus-only, but still pretty similar in concept) and it was a miserable failure
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State St was in freefall by 1979, because the middle-class people who shopped there had been steadily leaving the city for 3 decades prior, and Michigan Avenue sapped the luxury and tourist markets. The old theaters were also struggling, if not outright replaced by porno houses. Street crime, muggings, etc discouraged the few people who still wanted to come downtown. No mere pedestrian mall was gonna change the structural problems with downtown retail.
Daley got credit for re-opening State and putting in cutesy Victorian decor, but it was really a whole combination of things that revived State, from increased safety/cleanliness on the CTA and the Loop in general, to a revived middle class on the North Side, plus the creation of the Theatre District to bring back legitimate theater and musicals, and the recruitment of suburban big-box chains to take over the old department store spaces.
A pedestrian mall on the European example (or Times Square) creates its own demand for retail, because it is a place that people want to hang out in, to socialize, to people-watch, etc. I'm not sure such a thing is possible on Michigan (or State) but if it is possible, it will require careful management, policing that maintains safety without being oppressive, programming of events and activities year-round but especially in the winter months, etc.