Traveling with Christmas Cookies

I'll be leaving for Ireland the day after Christmas, and had originally planned to take Christmas cookies with me for my boyfriend and a few friends.

I want them to be as fresh as possible, but at the same time, I don't want to be baking on Christmas night.  Do you think if I made them tomorrow (the 22nd) and sealed them they'd be fresh-ish by the 27th?  What if I baked them and then froze them until it was time for me to leave for Ireland?  Any ideas?

Also, has anyone ever traveled on an airplane with home-made foods?  I'm thinking about putting them in a tin and checking them in my luggage, but I was also throwing the idea around of packing them in a carry-on so they wouldn't get crushed.  Do you think the airline would have issues with me flying with a tin of cookies in my carry-on? (I'm flying with Aer Lingus from Dulles, by the way)

I may be over-thinking this, but at the same time, I'd prefer not to put all of that time into baking and packing cookies for everyone and then have them taken from me at the airport.

Thanks, and Merry Christmas!

Thanks for any help/stories you may have.

Always best to check food items that you don't need on the plane.  Also, best not to wrap anything, because it is likely to get unwrapped.

Zip lock bags (or ziplock containers) and then pop them in the microwave in a paper bag/kitchen towel for 20-30 seconds would get my vote...  Stuffing some kitchen towel in the tin/ziplock container should keep them from getting jostled too much.

You wouldn't happen to have one of those food-saver shrink wrap thingy-mabobs, would you?  If not, I think it would be ok to wrap them in plastic wrap, put them into a ziploc bag, and then put them into some sort of tin or tupperware in your checked baggage.  i could be wrong, but I think it's mostly fresh fruit and veg, meat, etc., that gets taken away.  I brought loads of food here with me from the states in my checked baggage and they didn't take anything. 

I've brought homemade cookies on the plane before and they ran it through twice to check out what was in my jar, but it was fine.