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Regarding the development of the south loop west of Clark: am I the only one who thinks that area is just going to be a confusing hodgepodge of random-ness and dead end roads?
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I certainly wish it could be better, but I'm not overly concerned. There actually won't be any dead ends once it's all built out, though there are a few places where the east-west streets don't line up. Roosevelt and Polk will go all the way through, as will Clark and Wells-Wentworth. The offsets in Ninth and Taylor are regrettable, but shouldn't be impossible to navigate. Remember there are similar offsets along North LaSalle Blvd or Broadway in Lakeview.
Only in the US outside New England do we think a street network is the same thing as a gridiron. So long as the network is continuous and reasonably dense, it shouldn't be unworkable.