I would suggest that you rent for a while. Take your time and get to know the various neighborhoods in the city before making the commitment to purchase. There are a few really great posters on Trulia fromt he Chicago area. Read some of their threads. You can do a Member Search by area, read what they write and see what areas each covers.

I would rent for now. Buy a foreclosure property if you want to own real estate. You can rent it out and take the depreciation. The market wont bottom out for a while and if your new to Chicago, you would be better to check out the communities in Chicago proper or maybe a neighboring suburb. Bill in Woodridge.
I am not a broker but my wife is sick and I am just surfing the net. Good Luck.

Hi Robert,
Sounds like your credit,down payment, & income are very good. I think moving in the Bucktown/Wicker Park area would be a good fit for you (great neighborhoods & close to the Blue Line). You can never pick the bottom or the top of the market, but prices have come down and it looks like sales are starting to pick up (I don't think prices are going to rebound anytime soon, but it looks like the decline is slowing).

don't get more than 3 parking tickets or you get the "boot"
buy a city sticker for your car
don't pay attention to the crazy guy chanting and plucking his thumb from his mouth while glearing up at the very tall buildings, he's a regular
other than that, have fun, its a fun city.

Robert,

This is the perfect time to buy and it seems you know what you can afford. Existing home sales were released today and analysts predicted 4.85 million home sales for the month of February. The actual number was 5.03 million. One months figues is no pattern but it's an extremely positive sign for the market moving forward when you consider the doom and gloom over the past few months.
Any of the posters here on Trulia can be contacted to help you with your search around UIC and some may even have listings that they would be only too happy to show you.

Best of luck with your move and search. Ken.

thats a great start - the area right around UIC has exploded over the past 10 years, price varies, as in most neighborhoods - real estate is still contact sport for the most part - without touching the properties its hard to tell what works for you - feel free to reach out to me if you would like a better understanding of how I work with my clients, I would be happy to assist you with your search. Cheers Jim

Hello Robert-
Welcome! Jim is right. How comfortable are you in the city? There is so much to offer, it just depends on what your needs are. A short term arrangement would be beneficial in that regard. However, don't put off your purchase in hopes that prices will continue to decline. This is a great time to buy because rates are good and selection is high! I would like to offer the name of an agent I know who has been in the business since 1980 & knows the ins and outs of the city. She would be a great resource for you with the city market. Let me know if you would like her info! Good luck....

Robert, I would start with how well do you know Chicago, just like NYC each neighborhood has is own charm, pluses and minuses. If you can find a short term living situation which would allow you to get a better understand of what is attractive to you with respect to location, I believe you purchase will be wiser one.