Depends upon where you want to be. I was in the West Loop right off of Monroe. I was 4 blocks for 290 and 4 blocks from 94. It was quiet, I had good bars a block away or great restaurants on Randolph St. 4 blocks away and could walk to Michigan Ave in 20 minutes.
I also like Bucktown/Wicker Park area. Great restaurants and little shops. This is busier than West Loop but I would live there in a heartbeat. The best location describer is North/Damen. It depends upon the experience you want. I like these neighborhoods for living. Bucktown has great restaurants, nightlife, cool hip shops.
What used to be $2,000 can now be had for $1,500-$1,600. I just talked to my wife about it, who was a realtor and rented apartments as well.
Here's what she said. If you want to be downtown, downtown.....Streeterville (right around Water Tower) is the most expensive. Gold coast is a little cheaper and will run $1,250 (decent) - $1,650 for nice with great view. However, if you need parking it will run another $150-$200 a month. Gold Coast will be busy and you will be sharing it with tons of tourists....like yourself
Right now is low rental time in Chicago and you can find better deals if something is open. If you are serious about it, I can have my wife put you in touch with one of her realtor friends because a lot of them are doing rentals now. It costs you NOTHING. Basically, the landlord pays a commission of 1 month rent and then the realtors end up splitting it 4 ways. This is a no brainer, because it doesn't ever cost you anything, they look rentals up on the MLS and do all the work for you.
Bucktown would be $200-$300 cheaper than Gold Coast.