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I can offer my perspective -
I’m born and raised in Boston. Went to school (undergrad) in New England. Moved to Chicago for grad school and stayed except for 2 years when I moved back to Boston for work and was miserable.
Moved back to Chicago after that
I love Chicago and have zero regrets about it. I don’t miss that east coast abrasiveness or insularity. I miss my friends and family from Boston (and lol, the seafood and the mountains) but otherwise don’t really miss it. Everything is just a touch slower and the people way nicer. Cost of living is lower (especially rent).
There was a comment above about the academic environment of Boston. I guess ? Work is work. I work with a lot of smart people. Have some incredibly smart friends.
I don't know anyone who regretted that move. But if I had to guess, I'd say it's the kind of people who think anyone who didn't go to an Ivy League school is beneath them—and who brag about the kind of car their family driver used to drop them off at their private school. Or those who likes living in a prominent PhD and post grad student communities.
People who like Boston regret leaving Boston.
As someone who’s lived in a variety of places as an adult, I can say that Chicago is an excellent place to live. You get all the perks of a major city (good food, top-notch entertainment options, jobs, services) with few of the drawbacks. It’s not terribly expensive relative to other major cities, it’s safe if you choose properly, people here are kind relative to most cities, and you can find quiet areas even in town if that’s important to you.
I absolutely have had friends and classmates who left here because they thought they wanted to live elsewhere (usually wherever they came from originally), but I’ve never heard a single person say they regretted their move here.