Where you'd probably actually buy, with $800k burning a hole in your pocket, is Wicker/Bucktown, Lakeview, Hyde Park or Roscoe Village. If you were price conscious, you'd buy in Lincoln Square or Jeff Park.

$800k will also buy you a pretty fantastic house in Chicago. Of course, it won't buy you a house in the Loop, because houses don't go in the Loop. When people in the HN demographic think about the parts of Chicago they think are high-status, they're not thinking like a typical house buyer, who has kids, cares about the local schools, and wants a yard. Those people are buying in Beverly, Portage Park, and Jeff Park. Houses there top out at $800k; I had a sinking feeling looking at Redfin listings there (oh shit, am I wrong about this?) untiL I realized I had to drop the lower limit way below $750k to see all the available houses.

I assume this thread is about how hard it is to survive in major American cities on $300k/yr. I think you're generally doing OK just about anywhere in the US at $300k/yr, but I assure you you're doing well in Chicago making that.