My advice to anyone seeking an apartment in Chicago, forget The Reader, fuck Craig's List. Just come here to visit for a few days, drive around the neighborhoods you'd want to live in and look for nice-looking buildings with "For Rent" signs. Write down the phone numbers
Then call them up and set up as many appointments as time will allow. Do this in as many neighborhoods as you can. You'll find much better places for much better prices than you ever will in a newspaper or through a rental agent.
. I wish I could have let it sit for you and your friend. The people I ended up renting it to I think are going to be a pain in the ass with their "we want heat!" and "we want windows" bullshit. You didn't rent the taj mahal. There are plenty of cheaper options available in or around Lincoln Square if you go a little west of Western or north of Lawrence. Spending a day or two, as several people have recommended, driving around and looking for rent signs is the way to go. I'll keep my eyes open for you. I've been in Lincoln Square for about seven years and I'm really partial to it, but there are obviously a ton of great Chicago neighborhoods to choose from. If she's working downtown you might want to try finding a place near a metra stop. My wife switched to metra after all of the brown line construction crap and she now gets downtown in 12 minutes for $0.15 more each way.