Where there's a will, and demand, there's a way.
Right now there is still too much developable land in the South Loop so nothing will happen for the forseeable future. But combine diminishing vacant sites with higher property values, perhaps a new L stop (for the 78), and aging of the Dearborn Park properties to the point where there will be a substantial increase in maintenance costs, and eventually that whole neighborhood will be vanquished.
I'm pretty sure the city will have a lot of leverage with a developer who wants to upzone DP parcels that he plans to develop, one of which would be to force him to reconnect some streets that are currently cul de sac'd or walled off.
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