I think the best way to "get equipped" is to sit down and try and think of what sort of scenarios you can encounter daily. Chicago wind and snow, broken down car, transit strike, power outages, etc. Then given your daily patterns and distance traveled you should be able to outline a few highly likely scenarios that you would like to be able to respond to. Start asking questions about:
How will you get home from work? Should you even try and get home from work? How will the kids get home from school? What will the school do with the kids? What will my spouse do? Who can you leave messages with outside of the state in an emergency? Loads of questions like this for each of your likely scenarios. The plan is more important than the tools in my view. The tools and necessary skills fall out of the plan, but without the plan all you have is a sack of tools.
Take a real easy scenario at first...a Chicago blizzard while you are at work...toss in a power outage or two and then figure out the family plan.
Also you state that you carry nothing...actually you probably carry a load of stuff. Inventory your daily carry of money, the sort of shoes do you wear, your typical clothing set etc. Each of these items may need improvement based on the questions you formulate based on your scenarios. An office kit could be the result of this sort of review...better shoes or boots, overshoes, windpants, sweater, windproof, mittens, money, city map or transit maps, water.
Then the daily carry stuff can be improved as you see fit or supplimented with a car kit.
Being prepared for everything seems an huge goal, but being prepared for "known" things actually makes you about 100% more prepared for the unknown things.
To minimize blathering on endlessly, I do highly recommend Doug's main site for specific kit development....but strongly recommend a family discussion of events that will require some sort of thought on everyone's part, and then a development of a family plan along with some basic tools.
If you can stomach a bit more reading you can see more of my urban philosophy in two articles I have posted. These cover my kit contents and my attempts to evaluate scenarios that will affect me.....the absolute key is to develop you own skills and kits bases on your likely issues.
http://outdoors-magazine.com/s_article.php?id_article=171