Overhead: In order to fit in the overhead bin, your carry-on bag must not exceed 22" L (55.88 cm) x 14" W (35.56 cm) x 9" H (22.86 cm), including wheels/handles, on all of our aircraft types.
You will most likely have to check it. I've seen people try to get away with bringing a board on board and FA's make them check it at the gate. You may or may not have to pay for it, depends on the GA and FA for the flight. The only real way to avoid hassle is to either:
1) Take the trucks off, pack it in a suitcase, and check the bag.
2) Ship it down to where you're staying, probably taking the truck off first.
Also, don't skate around the airport. Guaranteed to piss off security.