Not at MDW but there are plenty such places and yes, some people do "get used to it". But there are studies that show that you increase health risks from such levels of noise even if you get used enough to it so that you can sleep through them. Search for increases in problems of cardiovascular health from car and plane noise.

And some people just won't really get used to it. I've lived near airplane noise and I never got used to it. I also don't sleep better with white noise. I sleep worse.

First time I was ever on a flight that landed at Midway, I was pretty freaked out by the visuals as we were descending. It's like ... "we're going to land on a house... we're going to Land On A House... we're going to LAND ON A HOUSE!! ... OMG, there's a runway <phew>".