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You couldn't pay me enough to live in Chicago (again) with a family. We actually moved there because the financial incentive was so good and we made a significant amount more than before. But we lasted less than two years before getting out. Some cities like NYC or LA could be really fun if you hit the right income spot, but in Chicago it was weird because it wasn't like money could have bought us anything we lacked. It's a relatively cheap place and we made a lot. The problem was simply Chicago itself and the absurdity of trying to raise kids there.
I'll add my observation around two cities that I've lived in, for ~10 years each.
Dallas: as a twenty-something to early 30 something, I lived the majority of my 10 years there in Uptown Dallas, which is probably the most urban and walkable of Dallas neighborhoods - bars, restaurants, all condo buildings, etc. There were no families there, at all. It was all 20's-30's singles or DINKs. The occasional 40+ divorcee. No children, anywhere, in Uptown or Downtown Dallas. Once you wanted to have kids and/or a proper house, you moved to the suburbs (most likely), or (if you had enough money) to one of the in-town suburban-style neighborhoods like the M-Streets, Lakewood or Preston Hollow.
NYC: contrast that with Hoboken/NYC, there are tons of families with kids living in tight quarters in urban neighborhoods. Hoboken is 50% families with kids under 10. Many Brooklyn & Manhattan neighborhoods are similar. The striking difference was that in Dallas the expectation was that you "age out" of the city, but that is not a thing here. You may move to the suburbs for cost considerations, but many people do that do so 'reluctantly'. And once the kids hit ~8-10, the odds of moving out drop considerably.
To get to my main point, I don't think I could live in the core of Dallas with my kids, because they would have no other kids in the neighborhood to play with. That place was designed solely for young, single people.
I mean, the whole "aging out of the city" thing basically originated in New York and it's absolutely still a (relatively big) thing. I do get the appeal of raising kids in NYC but I also recognize that given financial constraints and educational opportunities a significant number of parents race pretty quickly for the exits to raise their kids.
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