One of the major drivers of the rent vs. buy decision is the rate at which you expect rents to increase. Even if buying were more expensive than renting on a current year basis, rents go up while monthly payments on a home purchase remain constant. Eventually the cost of renting will exceed the cost of buying - and by an ever increasing amount.
Well, yesterday Zillow's May Real Estate Market Report was released and for the Chicago metro area it shows that while home prices declined by 6.8% in the last year rents went up by 9.1%. We've been watching this pattern for a while now and it's pretty phenomenal. The economics of buying relative to renting improved by 15.9 percentage points over the last year! And that's before factoring in the improving mortgage rate environment. This general trend is being repeated across the country but the magnitude is greater in Chicago than almost every other metro area.
I'm not a big fan of Zillow's home value estimates for individual properties but I do believe that their errors cancel out when looking at aggregate statistics like these.