Originally Posted by channa
That only takes into account the point-to-point distance between city pairs, not the routing rules. It's often better to fly to a closer city with an out-of-the-way connection than to fly to a further point along a direct route.
I guess I was thinking that more distant but cheap destinations also offer more routing options. Correct me if I am wrong but to use all of an airlines hubs as routing points I assume it is helpful to have a coast to coast destination. Note I said Helpful not necessary.
I still think the bestfares sort by price per mile is a useful tool.
My next suggestion would be to use itasoftware.com and look at their multi stop options for cheap fares for your favorite airline. You could even get fancy and apply the suggestions of previous FT threads about using semi colons for multiple destinations and within the 300 mile option.