Absolutely. Done it many times. I carry them when flying to skating events. I can replace underwear and clothes if my luggage is lost but not my skates on short notice.
I have relatively long skates (5 wheel, 13.5″ frames) and have a back pack that can carry them, a few skating clothes, helmet, and pads and still stay within the carry on size limits.
A friend carries a skate bag that is wider than the limit but it has never been checked for size.
However, don’t forget that there are limits on what you can have in the bag. No bearing cleaning liquids or aerosols like WD-40.
You might want to pack your skate tool into your regular luggage if it can conceivably be used as a weapon, along with the liquids.
You are allowed to also carry a computer bag (it doesn’t have to have a computer in it) or a purse to carry more stuff with you.
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Yes, but I would put it in a small bag/suitcase.
Carry on regulations-http://www.ifly.com/carry-on