I am not sure about Chicago is that expensive but I can very much identify with what is in this video as far as the greater NYC area is concerned. My social circle are in the high income bracket and almost all of them have household income of $400K or above, most of them significantly above. Once they have children as pretty much all of them do, the cost becomes very high. It is a choice they make but all of them, including myself, make the same choice. In blunt terms, the choice is to make sure their children lives in and attend school in an area that matches their social-economic status. But the cost of housing and/or private school is expensive. Since people in a similar income bracket pretty much make the same choice, they bid up the cost of housing of schooling and as a result, unless they are frugal in other areas, the level of saving they achieve is low relative to what one would expect given their income. In that sense I very much think the video is in touch with the experience of households in the upper-middle income brackets living in high cost areas.
From what I hear, urban/suburban Illinois is about the same price as other midwestern blue states like Minnesota, Colorado and Wisconsin. At least salaries are similar.
But I stand by my remarks that people in certain communities should simply feel on top of the world from being even able to afford to live there at all.
