Looking to move to Chicago in the near future. Why do so many apartments not have centralized air? I’m looking to buy a place but this is a deal breaker for me. I’m assuming it’s just the older buildings, is there a certain year where they began including them? Would make filtering my searches much easier...

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Anything built before 1950ish and not fully rehabbed is not going to have central air.
I assume you’re coming from the south? A/C is not anywhere near as common in New England and the Midwest as it is in the south - we just don’t need it that much. I have yet to turn mine on, open windows and my ceiling fan are plenty. Middle of summer def is hot, but I think most ppl probably are fine with a window unit for the 1-2 months you actually need it.
They also make pretty nice permanent wall units that you can install for much less than fully installing central air. That’s what most of the rest of the world has since central A/C is not really a thing in most countries.

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