I haven’t ever been to Columbus, Cincy, or Minneapolis.
Based on articles I’ve read, Streetview visits, pics, and my knowledge about infill development, though, my hunch is that Minneapolis wins.
It has the most high rise construction, lots of urban infill, and progressive policies towards zoning such as eliminating SFH zoning.
It may have less prewar fabric than St Louis or Cincy but urbanism doesn’t have to end there.
I also think that Milwaukee may deserve #2 status. I say this because it may not be as large as some other cities, but it’s extant urbanity is quite impressive. Plus it now has a streetcar and it has downtown-to-downtown rail connections direct to Chicago, with plans underway to increase said service.
St Louis has some wonderful building stock but it seems too disconnected unlike Milwaukee which, like Chicago, has nearly contiguous urbanity radiating out from downtown.
I won’t comment much on Cincy but it seems like its big claim to fame is OTR which seems wonderful, but not encompassing enough, it would seem.
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