File whatever you want. It is an exercise in familiarity with the
airspace to file a route.If I don't file direct, I usually file VOR to
VOR, I don't like refrering to airways, that way I learn where the
VOR's are. But nothing wrong with filing, and flying, direct. After
all, direct is the shortest route. The CFII gods are all hung up on
"routes". (LIke the air on "Victor 81" is somehow "better" than other
nearby air). And like in "yeah we took Victor 491 ALL the way to
Butler". "OOoooh, I am sooo impressed". I suppose that was like way
hard to do, LOTs harder than going direct or some OTHER less prestigous
route like VICTOR 13 or Victor 69.

I was in Gary Indiana and had to file IFR to get over to Moline and
onto Colorado. This is through Chicago airspace, very busy. After
carefully previewing my route, talking to FSS, I filed a nice looking
route. I was given a clearance for a different route, and when I became
airborne, I was cleared for something else again. Nice thing was they
gave me my own controller, no one else on the freq. He wanted to know
all about my Husky.