While it's true that prices have adjusted downward in many Chicago areas, as Nick said, many sellers who feel they didn't meet their 'bottom line' with their sale are finding they are able to upgrade in ways they probably would not have been able to 2 years ago, so the 'loss' ends up being a gain.
Make sure that you enlist the help of a good buyers agent. In River North & the Loop there are several buildings that have problems that are not clear on first look. For example, high foreclosure rates or high rental concentrations, etc. A good buyer's agent will be able to inform you of those issues and get you a good deal on the buy side. The way mortgage rates have been waxing and waning, you may even be able to improve your mortgage rate.
Broker - RE/MAX Signature
I think a lot of people jumped the gun in terms of deciding to purchase in RN rather than look in other areas and I think prices are certainly less insulated here than they are for the more established part of the near north area- the Gold Coast. Many of the huge high rises are struggling and I am seeing a noticeable jump in foreclosures here too.
My advice- sell your condo for what you can get for it and then turn around and upgrade for $.80 on the dollar compared to what you would have paid when you bought what you have now. The area- like the rest of Chicago- will make it through this crisis but there just simply hasn't been a buyer's market like this is a long time so take advantage!
Just saw a foreclosure at 300 W. Grand listed at $209,000- It had 15 offers on it in one day and sold for over asking price.