Speaking as a fellow Wisconsinite, I've made that type of drive on numerous occassions, and it isn't that bad. However, I will second the suggestions of the others here -- break it up. I have found it much easier (and less draining) to leave immedaitely after work, drive until 1-2 am at the latest, wake up at 7-8 am and then finish the trip. In your case, I'd probably shoot through central Illinois and stop over in Carbondale (college town) which should take you about 5.5 to 6 hours barring construction. You could shoot for Memphis, but that's a bit long for a post-work drive.
If you've never driven through southern illinois, be prepared for miles and miles of flat corn fields -- very boring (we call them flatlanders for a reason).
As for police, Illinois troopers are not as bad as Wisconsin troopers, but they have been pushing construction zone speeding big-time (including camera vans that issue tickets via mail). I've heard that Missouri troopers can be tough, but have no first-hand knowledge. From there, you're on you own.
If you've never driven through southern illinois, be prepared for miles and miles of flat corn fields -- very boring (we call them flatlanders for a reason).
As for police, Illinois troopers are not as bad as Wisconsin troopers, but they have been pushing construction zone speeding big-time (including camera vans that issue tickets via mail). I've heard that Missouri troopers can be tough, but have no first-hand knowledge. From there, you're on you own.