wrigley
Full time employment: Posting here.
An interesting comparison-
We are retired in one of the distant suburbs of Chicago. A couple we are friends with had retired from the same company about the same time, lived only a mile from us. our financial situations were/are very similar. They did the math carefully and calculated that their overall cost of living would be about $500/month less near Phoenix (Chandler). So they moved, partly because of family there.
After they'd been there about 3 years, I asked about the cost of living comparison. They said it was a tie, overall living expenses there are the same as ours. Our high property taxes are offset, as others said, by no state tax on pensions/SS.
DW and I enjoy spending a couple of months each winter in AZ or FL, but don't want to live there.
YMMV
Chicago and the surrounding suburbs are great places in the summertime. You are fortunate in that you can escape during the winter months for warmer climates which makes the small amount of time spent in the Illinois winter bearable. I have family in Naperville, Park Ridge, Tinley Park, Darien, and Chicago. 24 years ago when I retired form the military my plan was to move back to Chicago to be near my family and where I grew up. It didn't pan out at the time and I was disappointed. After living in Florida for the past 29 years, I'm glad the Chicago move didn't pan out. As my siblings age they are all planning an "Illinois Escape" to warmer climates with the exception of my mother. She jokes that she will be buried in the frozen tundra of the Chicago area where she was born. "To each his own."
Mike