Your agent should be able to answer these questions for you George.

There are many reasons for people to list their home for sale regardless of the time of year. On of the most obvious is job transfer. These are generally highly motivated sellers and a great opportunity to find a good value. Since there will always be significant inventory to choose from in a city the size of Chicago perhaps the better question is whether you have your financial ducks in line to jump when you do find that perfect property? Many agents will not show homes to buyers who have not been pre-approved for a mortgage loan. Consider using my free inline prequal calculator to estimate the loan amount you are likely to qualify for and then submit it to my secure online for pre-approval.
http://www.gregzaccagni.com/WhentogetQualified

George,
It sounds like you're concerned about having enough properties to choose from and ensuring that you get a good deal. Surely you're aware that virtually the entire country is in the throes of a buyer's market? Ask your agent to calculate for you the absorption rate for Bucktown/Chicago and you will have the answer to your question.

I can understand how buying in the off-season has its advantages.

I'm really trying to get a sense of whether or not I can expect to see new listings come up over the next several months while I'm in temporary housing, or if the apex of buying season is already upon us. I've been scouring the listings and I'm not seeing a whole lot of new properties (in my price range, desired area and features, etc). Temporary rental housing is not an ideal choice for me, but if the supply of properties typically continues to replenish even into the Fall it may be worth toughing it out until then.

So, my refocused question is:

Generally speaking--

Aside from the people selling properties because they have "no choice" (e.g., distress, job-relocation, etc.), do people in Chicago continue to put their homes up for sale (new listings) when the weather starts to turn for the worse? Or do they hold off until the next selling/buying season?

I know this is a tricky, loaded question, but I'm fairly new to Chicago and the quirks of the RE market here.

(BTW, I do have an agent.)

I am an agent in Chicago and "off season" is the prime time for someone that has nothing to sell. You will pick up your best deals due to people afraid that they will have to wait til spring to sell. Good Luck!

Absolutely! I agree! And in all honesty, it's EASIER to find a great home in the "off season", as you called it. Only true gems exist. I am also a KW agent. I'm in the Barrington area and I have a client that is currently looking in the Bucktown area. There are some great deals out there!

You just have to know specifically what you want and or need. And how much you are willing to spend. And then, go after ONLY that.

If you need a home in 3 weeks, unless you are prequalified, you may seriously want to look at renting or rent with option.

If I can help in any way, please feel free to call or email me!

Can't tell you about Chicago, but in general there are always homes available, and buying "off season" is sometimes easier - with less buying competition. I assume you have an agent? If not, please email, I'd be happy to refer you to someone. VChrisner@kw.com