The more detailed post I promised earlier.
When I fly to a convention, in particular Gen Con, I am typically packing the following:
My backup builds for Druid, Paladin, and Fighter
Some random tokens for the rest of the Group
Space to return with about 200 pulls from treasure + additional tokens
X-Wing Miniatures (both imperial and Rebel fleets)
Battletech Miniatures (24 Mechs)
Infinity Miniatures (~20 miniatures)
All of this goes into a Battlefoam 432 - I use this as my personal carry on and it goes under the seat in front of me. Its slightly bigger than I like under the seat, but its the best solution I've found to carry this much stuff.
My actual Cleric build, along with all of the Party's TEs go in an OPTIMA token binder I got from Trent, and this goes in my roller suitcase with my clothes and that goes in the overhead:
www.trenttokens.com/collections/trent-tokens-binders/products/token-binder-optima-f-ringbinder
TSA didn't complain with the tokens neatly arranged in the binder in my suitcase, or neatly stacked in the battlefoam bag - your mileage may vary.
If you don't need to take that much stuff, I recommend bringing a smaller bag with your tokens and keeping it under the seat in front of you. I wouldn't mix it in my roller bag, and I wouldn't risk checking it, unless I was running builds of rare and under tokens.