We've done the trip a few time from the northern suburbs. I personally like to leave around 9:00 pm on a weeknight. We have a 3yo, so we put in a DVD, he watches for a while, then falls asleep. I drive through the night, and the last 2 times we have stopped in Chattanooga. There's a pretty nice mall there right off of 75 - the name escapes me at the moment, but it's "[something] Place". Leaving at night, we have gotten there around 7-8 am. We eat a nice breakfast at the Craker Barrell, then head over to the mall for a couple of hours (They have a good
Disney Store in there). My wife drives for a while after that, and then we try to make it into N. Florida before stopping. Last time we made it to Gainesville. It makes for a long day, but by stopping at 6 or so, it gives me enough time to recooperate by the next day, and only leaves a short 2 hour drive to WDW. There's lots of Wal-Mart's along the way, so we usally make a couple of stops there, as well, just to stretch our legs. Seems any town along the way with a population of 20,000 or more has one.
We do most of our planning along the way as far as where we'll eat, get gas, stop for the night, etc. Just watch the road signs, everything you need is on the billboards.
We're doing the same plan this year in Sept/Oct, except heading to Clearwater Beach for a few days before WDW. I really don't mind the trip, especially with the DVD player. Our son has made 3 trips - 2 by driving and 1 by air, and overall we thought the drive was less hectic, especially if we're not pressed for time. My wife hates to fly, and it really took away some of the fun by her being so nervous leading up to the trip.