Surveys like these always highlight how Chicago is underrated: New York: $275 Los Angles: $236 Chicago: $112 San Francisco: $459 Washington, DC: $164 Housing here is comparable to places like Richmond or Raleigh, except it's got the public infrastructure of a world-class city with 10 million people. Even if you live in the suburbs, you can take the extensive commuter rail system straight to downtown.
The weather is a deal-breaker for a lot of people, I suspect.
It's like buying a brand new car. Sure it's nice and cool looking, but eventually it becomes just a transportation option to get you from point a to point b. Or it could be like that you're going to buy a house with a pool. However, you'll rarely actually use the swimming pool.