Home of the Sears Tower, hot dog vendors, and da Bears, Chicago has a lot of stuff that you'll never see in LA or NYC. Chicago is also really big (and have you heard that it's windy?), so it has a heck of a lot of space to spread out buildings across miles of land. Granted, it's not all nice space, but it's space nonetheless. This is very good for you, because it means that there are tons of places to find your dream apartment. We'll show you how to get the job done quickly and correctly. Besides, how can you go wrong living in a city where 4.6 billion Oreos are made every year?


Chicago offers a wide array of housing. While New York is expensive no matter where you go, Chicago gives you a lot more options. A good way to find your upper limit for housing costs is to divide your monthly net (after tax) income by three. If this figure seems unusually low, you have three options: (1) make more money, (2) consider living in a less expensive area, like the Far North or West Side (see step 2), or (3) save money on rent by finding a roommate.

Maybe get yourself a roommate

If you decide to get a roommate to lower your housing costs, you can choose a friend/acquaintance yourself or you can use a roommate agency (such as Roommate Click). Either way, you must carefully choose your roommate or you will rue the day you opted to bunk with someone else. Obviously, not all strangers make good roommates, but less obviously, not all friends make good roommates. There are some people whose company you might well enjoy during the day, but who would drive you crazy if you lived with them. In order to exclude such unsuitable people from your life, you should ask all potential roommates the following questions to assess your compatibility:

  • Have you ever had a roommate before? What, if anything, bothered you about your past roommates?

  • Do you have a boyfriend/girlfriend or other friend who will be staying here frequently?

  • Are you promiscuous? (Do not be afraid to ask this one. You probably don't want strange people sleeping over a lot, and if you explain that this is the reason you're asking, it will establish what you consider unacceptable ahead of time.)

  • Do you smoke? Drink? Do drugs? If yes to any, how often? If not, why not? And if not now, when?

  • Do you stay out late on weekdays?

  • Did/do you have any credit problems?

  • Do you have any pets?

  • What is your occupation?

  • What do you like to watch on television? What music do you listen to?

Whatever you ask, in the end you should feel very comfortable with your future roommate. If you do not, you are taking a huge risk. Also let your potential roommate know about some of your weird living habits (such as how you like to walk around in the nude); the goal is to create as little friction as possible.

One last note about roommates: try to arrange it so that your roommate co-signs the lease. If your name is the only one on the lease, then you shoulder the entire burden of responsibility for the apartment from a financial standpoint. If your roommate loses his/her job (and by extension, a steady cash flow), you'll be stuck paying his/her share of the rent. Then you'd be angry, poor, and kicking yourself for not following our sage advice.