As a buyer, you are in a fantastic position and I am pretty confident that anyone who is educated on the economy, the real estate market, etc. you ask would tell you the same thing.
If you have at least 3-5% to put down, have GOOD credit (700 or above) and know you are planning on staying in your property for AT LEAST 3 years, then it truly is time for you to become a homeowner.
When you ask how the market is doing, it's down. It's down everywhere. Just remember, as a buyer, the market being DOWN is good for you.
Let me give you some food for thought... over the past 100 years, the market has gone up and down in cycles. On average, in a down cycle, the market has been down by 4% (again this is an average). Currently, on average we are down 7.9%, which would put us down by double than the average amount (I was a math major;). The point is that if you are "waiting out the market" or "waiting for the market to go down more"... you shouldn't be. NOW is the time to get the great deals.
That's my two cents! I currently have a listing in the Loop/west loop at 625 W. Jackson. My seller is listing at the same price he paid for it over 2 years ago, and he has put about $10,000 into the property. He's losing money but he has to sell as he is moving to LA. Again, now is the time for the deals.
Good luck and if you haven't found the right place yet, I can send you over some great properties I know of in the Near West Side neighborhood. - Sierra Bloom Imwalle - Jameson Real Estate - email@example.com