I currently live in New York City, but my job is based out of Chicago. On its own merits, I don't find Chicago much more or less appealing as a place to live (though I've not spent much time there, so this isn't a very well-informed opinion), so this may come down to whether my dispreference for remote work outweighs the inconvenience of moving and the fact that many of my friends and family are in NYC.

Related: https://manifold.markets/Forrest/will-i-live-in-chicago-at-the-end-o