You've been looking for a Chicago condo for months now and it seems like you just can't find anything decent. All the condos in Chicago seem to be either overpriced or in pretty terrible shape. Well, there's a very real reason why your condo search seems to be going nowhere.
As I've pointed out before Chicago's home inventory is running very low as a result of stubborn or broke sellers refusing to sell at current market prices. In particular we track the inventory (months of supply) of 2 - 3 bedroom condos in Chicago and it has been trending down for over a year now as you can see in the graph below. In December inventory levels hit a new low for that time of year - the lowest level in 6 years. That's good news for sellers and bad news for buyers.
With so little inventory on the market it's no wonder you can't find what you are looking for. And don't forget that 45% of all Chicago home sales are distressed properties so a lot of what is out there is pretty beat up.
If you are interested we maintain a page of on our Web site that contains this condo inventory data along with numerous other Chicago real estate market data all in one place.