How is this in Detroit:
Attachment 18809
any more of an impediment to walking or development than this in Chicago:
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Or this in Chicago:
Attachment 18810
You have to cross that ^^^ to get to the West Loop, especially its Restaurant Row at which starts on Randolph at Desplaines or so and heads west, over the highway for several blocks - it straddles the highway. 90/94 certainly is not breaking anything up, nor is the river breaking up River North/Gold Coast/Streeterville from the Loop. I think in some cities, like Houston, it does rope the city in, but that's not the case in Chicago or Detroit [[or other cities that structure their highways in such a manner).
That's exactly why it is thought that the new Red Wings arena and $650M entertainment complex is going right across 75 from Foxtown - it's easily accessible to both midtown and the rest of downtown. Walkable, bikable, driveable, easily.
Better not go to any major city outside of Chicago and the Northeast then...LA, Houston, Dallas, and Atlanta require cars, fwiw.
Just use Uber. It's newer here in Detroit so I haven't used it but my friends back home in Chicago love it. It must have started up out there after last summer because I don't recall hearing about it at all before I left.