I go back and forth about taking my CPAP with me when I travel. I'm currently back in "take mode." My normal setup is a Tom Bihn Brain Bag and a 22" Kirkland roller. I picked up two identical medium "stuff bags" from REI. One of them gets the cables and tubes, that goes into the 22" along with my toiletries. The unit itself (one of the smaller ResMeds, and I don't use the humidifier) and goes into the Tom Bihn next to my laptop, and I have the other stuff bag rolled up in one of the TB pockets.

I have to open the TB anyway to take out my laptop, and I find that both the laptop and the CPAP fit in the same tray for TSA. About once a year, somebody at TSA gripes that they should be in two bins, and it takes me an extra 2-3 minutes to clear.

I'm going to be doing some travel in Europe soon, where even a full Brain Bag may cause some issues with an overzealous flight attendant, and I'll be checking my suitcase. For that, I've ordered and am waiting on a RedOxx Extra-Small Aviator Bag, which I think will handle my CPAP, laptop, cabling/power, medications, and a fresh shirt and underwear. That plus my Scottevest should suffice.