I get a lot of questions about the housing market on this blog so here is some information on making the best decision on your dream home:
First of all - find the best mortgage that fits your needs - find a mortgage broker or work closely with your bank. If you've been with your bank for more than a year, they should be willing to work with you to find the best rate available - so make them earn their money - that's why you're banking there, right?
Once you know how much house you can afford - find the right neighborhood - remember that what worked for you at twenty probably isn't a fit for you at forty - things change - you get tired of mowing lawns, replacing gardens, and repaving driveways - you might be ready for a condo, or a townhouse in an area where the outside stuff is already taken care of - lots of people tell me that they aren't into outside work, so don't let that bog you down. This is Chicago and with all this inventory the perfect fit is right there.
Select the building that fits your needs - do you need lots of space? have you measured the furniture? how is the piano going to get inside? how close is this to the expressway and how many grocery stores are in the area?
Make sure the lay out of the unit fits your needs - you're going to be walking around the place for a long time. Are you certain that you want a place with the bathrom on the opposite side of the floor plan? If you want the kitchen to be the focal point, make sure you don't select one that won't fit everyone in it. If you are used to falling ino the living room, make sure it's as comfortable as you need to make it yours.
Make at least three trips to the chosen place - once in the sunshine, once in the rain/snow, and once at night. You need to get a true feel for how the place looks and how the neighborhood looks in each situation. That way you know what you are getting into - if the neighborhood is pitch black, the garbage isn't collected, or the clubs explode as soon as the sun goes down, you need to know it before the moving van gets there.
Work with your realtor to create a timetable and a plan - you should make sure the electricity doesn't go off a day before it's scheduled to and that it's on in the new place at least one day ahead of time.