Like Bob Z I have been a southsider all of my life. Most people that work downtown utilize public transportation(Metra trains). Driving downtown is brutal no matter where you are coming from. You will miss your 20 minute commute. Mine is a min. 1hr each way.
Housing costs in the north and northwest suburbs are higher than the south and southwest. The western suburbs seem to be in between. Be prepared for high property taxes no matter where you go. For a nicer home you are in the ball park of 350,000-450,000 s, sw, and w, 500,000-600,000 nw. I am a building/fire inspector for a large nw suburb, so i see what these houses are going for. New homes in the 800,000-1,000,000 range is not uncommon at all. Taxes can be 5,000 -15,000 per year and even higher.
IMO, they can keep Chicago. Trying to convince the wife to move west.
What is your line of work?