WI west of Madison and in the north has always been similar to corresponding parts of MN, and continues to be.
However, Milwaukee was never really like MN since its more of a rust belt city while MN doesn't really have a rust belt. Some might argue that Duluth is rust belt, but it really isnt as it was always about resource extraction rather than manufacturing and MN successfully added tourism to its base. There really is a line in WI between the rust belt and dairy country (which also includes tech).
Incidentally, pre-2008, 538 ranked MN closer to WA than WI, though WI's closest state was MN (
https://fivethirtyeight.com/features/state-similarity-scores/)
