They all have great potential.
All have several elementary schools; there are distinct differences and yet they are very similar and have a lot of crossover; in any event come high school the boys mish quite well.
Both offer good high schools too; even though people do send their boys away the options are there.
Chicago is bigger and doesn’t have the same small town feel, though it’s still not exactly NY. You’ll be able to get a lot more house for your money in the other cities. There is the feel among older people that when they see a strange face it’s a bit disconcerting because you still expect to know everyone.
I assume you have good parnasa opportunities in each city?
Is proximity to extended family a factor?