I have done the drive from the Twin Cities many times for many different reasons. I love the drive and when there are two or more adult drivers we drive straight through. Otherwise, we stop around Chattanooga for an overnight.
There are two routes I take depending on the time of day we leave. One is I-94 to I-90 towards Chicago taking I-290/I-294 around west side. I then connect up to I-80/I-94 on the south side for a quick jaunt over to I-65 in Gary Indiana.
Another route through Chicago I love to take late at night (because I love the city lights of Chicago) is to stay on I-90 right through the heart of the city. I then catch I-65 right where it starts in Gary Indiana. Either way you go you connect up with I-65.
Take I-65 south to I-24 in Tennessee, then I-24 east to I-75 and then I-75 south through Atlanta down to Orlando. The big issue with this route is traffic around Chicago, Nashville, and Atlanta. It can be very heavy depending on time of day and day of week. There are also the tolls in Illinois.
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The other route is I-94 to I-90 to I-39 outside of Rockford, IL. Take I-39 south through Illinois to I-74 and then a quick jaunt to the east on I-74 to I-57.
Take I-57 south to the start of I-24 and jump on I-24 east through a bit of Kentucky and then across Tennessee. Hit I-75 south and take it through Atlanta and down to Orlando.
Issues with this route...Illinois seems like it never ends! And, traffic around Nashville and of course Atlanta. Again, depending on time of day and day of week you can pick your way around Atlanta if you'd like.
Another note...traffic hauls butt on some of the freeways, most certainly stretches of I-65, I-24, and I-75 especially south of Atlanta. Unless you like to play "keep up" some of the traffic zipping by (especially semis) can unnerve some people. It doesn't bother me, but some of my passengers/co-drivers have commented about it...
As for road conditions, you can check on any construction by using the interwebs. Each state has a department of transportation website that lists posted construction areas.
As for weather, mid-November should not be too bad for driving. I plan on driving down around the same time.