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In short... It depends on the airline. However, following is some explanations which could assist you in taking your next steps. Tried and tested..Some airlines will allow you to take on a skateboard as hand luggage but only the skateboard, no additional bag. We've all seen the viral clips of people focusing their decks at check in desks due to not being able to take it on at the last hurdle, despite travelling with it on the inbound journey.
Ideally your first go to will be a checked on bag (hard luggage) to put your board in, if no checked on bags & your only option is to smuggle it on continue to read...
Confidence is key, when building your rig up to conceal/camouflage your skateboard into your luggage consider matching the colour of the fabric used to match that of your backpack, this will avoid attracting too much unnecessary attention. be sure not to spark up random conversation about baggage allowance or anything to do with carry on for that matter of fact at the check in desk nor security. Ideally put the board in a separate tray upon going through security and the re-rig it up on the other side ready for the final desk jockeys at boarding. See below some examples from a recent successful smuggle from C**nor (MAN > LPA Return) using the hand luggage rig up suggested. Some airlines will allow a skateboard as separate carry on but ensure you've checked beforehand and ideally have it in writing to save any T&C's jousting when at the airport.
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This method is ideally executed using a backpack with skate straps to hold all in place, elevate the rig with a cover up shown below. Click here for suggested skate bags if you're in the market for one. Worst case if you're pulled up on this you'll either have to lose the deck or pay extra to have it checked on. I've found if the staff are nice enough & you give them the right attitude they'll work with you to get your board on the flight.
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I tried a rig up myself on the checked bag that wasn't big enough to house my deck, by shrink wrapping it to the outside of the suitcase i thought it would go unnoticed with some distraction small talk at check in, I was wrong. The bag with rig up in tact was on the scale with label applied so i thought i was on the home straight but she said that's gotta come off. Luckily shes was super sound and said she'll have it checked on as "abnormal sized baggage" at no extra charge (this does cost additional but she wavered it at her digression). See below the failed rig up but which resulted in the deck being "upgraded". The deck wasn't coming with me on the return journey so this worked okay for me.
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