Small world - we live about 2 miles from Midway.
Anyway, we usually leave after work on Friday (anywhere from 6-9 pm depending) and drive straight through too, weather permitting. In 2008 we had to slow things down quite a bit due to weather but we're pretty experienced winter drivers so it wasn't a problem. Most times it's the other crazy drivers around us that worry me.
Enjoy your trip and drive safely. We are leaving again on 12/19 so I'll be sure to post about road/traffic conditions when we get back.