You can't have high taxes and bad weather and keep people around in 21st century America.
On the other hand you can argue that Chicago has picture perfect from May - October. The reverse of Phoenix essentially. Also there are no natural disasters that could destroy Chicago unlike many of these sun belt cities.
But the extremely harsh winters is literally the reason I never made the jump to move to Chicago.
IL, NY, it is sad.
Illinois won't be trending Republican because a lot of Republican voters are moving to AZ, FL, NC, NM.
Somewhat mitigated by a loss of black population but overall the state is shrinking and becoming more Democratic at the same time.