This past weekend, my girlfriend and I were talking about visiting her grandmother in TX. Grandma's health isn't what it once was and we want to get as many visits in as possible.

I raised the idea of a Chicago->Houston road trip and, to my delight, she seemed very receptive to the idea. She had done it once before, accompanied by a friend from college, and said it would be fun to do again. She's not as seethingly, bubblingly anti-TSA as I am and I don't think she entirely approves of my flaming disdain for the front-line TSOs (though she doesn't seem to object to my wanting to see Pissy and Nappy living in cardboard boxes, fighting off local stray animals in order to be able to eat that day) but when I mentioned that a road trip would be a nice F-U to the TSA she didn't disagree.

All this having been said, I've never embarked on such a road trip before and am a bit lost at where/how to start. What precautions should I take with regard to looking after my own safety since I won't have the all-powerful all-knowing all-wonderful TSA to do it for me? I'm thinking stuff like having my car checked out beforehand or even just renting a car, how long it's safe to drive in one shot, "scam-the-out-of-towners" schemes I should be aware of if we're eating/staying in a town in between, that sort of thing.

And on the lighter side, any good places to stop between Chicago and Houston for good sightseeing and the like?