I flew between canada/US during christmas, took my board strapped to a backpack as a carry on (and checked a bag for clothes and such), no problems!
I would suggest you just check a bag with your clothes, I think I heard somewhere that they count a skateboard as a second carry-on item even if its strapped to a bag. There might not be enough room in the overhead if you try to bring all your clothes, a backpack, and a board on the plane.