You mention Uptown and 60640. This zip code includes parts of much pricier Andersonville and what some might call Ravenswood North. There are huge differences in demand (and rent/buy) here versus what many would call Uptown (east of Clark, south of Lawrence, north of Montrose)
One factor to consider when buying is do you want to take risk? There are lots one bedrooms to buy and people have been waiting a generation for Uptown to change.
A good option to consider is buying with the intention to rent after you move out, but you need to check the following:
Are rentals allowed and how many, and is there a wait list?
What are your monthly assessments? Do not buy a place with high monthlies (you should never be over $300 even with heat for your budget)
Are you willing to deal with a renter?
I saw somebody mention about renting being easy. It is true! If you can afford the rent, and you don't know what you are going to be doing in a few years AND you are risk averse, just rent and forget about it.
But if you buy a condo at the lower end of the price spectrum, and current rents exceed your total monthly payment, you have a relatively safe investment.