I am often asked, "when is the best time to buy?" In Chicago, this is a relatively easy answer, WINTER! Yes, you read that right. It is best to buy when its freezing cold, 3 feet of snow on the ground, with skin piercing winds. OK, a little extreme in that last sentence, especially as mild as our winters have been in the last few years. But let's think of our winter season as a typical one where it is cold and not one where were wearing shorts to Christmas dinners.
During the winter time, a few things happen. 1) The amount of buyers in the market goes way down and 2) seller's that are just "testing the market" go away leaving only real sellers in the market. The two biggest selling and buying season in Chicago are spring and fall. This is when the most buyers are out there and when most sellers will list their properties. Once the holiday months come around, many of these people put things on hold until spring. It's not a lot of fun to look at properties or deal with showings during the holidays. But that is when the best opportunity for deals exist.
When the holidays come around, seller's that tried testing the market will pull their properties off and wait until spring before relisting. This leaves any properties on the market as people who really need to sell. These sellers know its annoying to have to leave for showings in cold weather and are only doing so because they truly need to unload their place. Plus many need to sell before the end of the year for tax reasons. For these reasons many more sellers are willing to negotiate off their price and are willing to take less just to get the property sold.
On top of this, the buyer pool goes way down so your competition for these properties is not as tough as it is in spring and fall. People buying usually do so during the warmer months because that is when things like leases are ending, its more fun to look during the warmer months, and there is typically more available to look at.
So keep in mind, if you really want a "deal" like everyone says they do, look during the holidays and winter time. Don't wait until the weather warms up or you will likely be paying more than you want to.