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Most hardcopy atlases have a "distomap" in the back of them. I used to use that all the time when I was a booking agent to route my bands. It is basically a map of the US with a sort of "connect the dots" pattern to all the cities in the US. The lines are marked with both distance and time. Make sure you use the distance rather than time because the time doesn't take into consideration areas with a lot of traffic.
By the way, the road atlas I used was Rand McNally and they used to come with a CDRom called "Trip Planner" on it. It was pretty cool, but totally worthless for what I needed. See if you can find a copy of that program because it looks like what you're after.
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