Hauling a regular pillow

Since you check the roller bag, its size does not matter much: would the pillow fit in one half of a regular suitcase?
Otherwise my first thought was vacuum-packing the pillow, if its material allows for it, but that only solves the first leg unless you ask to borrow a vacuum from housekeeping everytime you leave a hotel (which would not be an unreasonable request).

I’m not sure what type of pillow you have or how much it can be compressed but do you have a light weight nylon bag that has an open outer sleeve that can be put over the raised handle of your carryon for getting on and off trains using one hand? That might be a way to transport it when you are on the move.

All kinds of sizes and solutions like this https://www.baggallini.com/packable-tote-bag/PTB493-BG.html

Haul it in another bag as your carryon. I would put it in a bag with back pack straps and carry on and off trains on my back; and your other bag you can roll it until you need to pick it up getting on and off trains.

Great tips, thanks.

Look at Etsy under backpacking pillow, as those are compact and perfect for travel.

Your title mentions 'regular' pillow, but you also mention a a specialized pillow. Ifnyou need it for vertigo, then I wouldn't want to be ruining my vacation by not bringing the specialized one. If it is a strange shape but would still fit in your regular suitcase, I would pack it in that suitcase, then start adding clothing around it. It is easier to find smaller tote bags to accept clothing that a second suitcase for just a pillow.
If you have tested things, and can just use a regular pillow, I suggest laying it flat in the suitcase and using packing cubes on top of it. I have packed a pillow in a compression bag before, but it becomes stiffer and more unwieldy. I find it shrinks well, and allows me to ake better use of packing by laying it in first, then 'comoressing' it with packing cubes and other items with weight.
It is all annoying if you are moving lodgings often, but better than recurring vertigo.

I'm with the others regarding, uh...squishability. I'd look at the compression bags IF that would work with your pillow. I've got the size that will fit in my carry on and have used it for bulky outerwear. It's the kind of compression bag with one-way valves that does NOT need a vacuum to seal it - you just roll the item to get the air out and create compression.

BTW, RS guide Sarah Murdoch does packing workshops for Rick and SHE takes her own pillow, lol!!

Yes it is a specialized pillow but somewhat regular size. It’s U shaped. I think the idea of a lightweight bag that can slide over the roller handles on the roller bag might be the trick, but putting the pillow in the main roller bag and then just clothes, etc. in the lightweight bag. Since I am also carrying a backpack with stuff like my iPad maybe I will look at Amazon and see if I can find a lightweight slip over bag that can be checked on the flights. Dunno, that’s why I am asking all you creative people! Thanks.

Right now I am taking a break from my physical therapy neck exercises.. The idea of sliding a smaller bag over your roller handles sounds like an easy fix. The consequences of not taking your pillow sound severe. How often will you be moving on and off trains? How often will you sleep each night? I’d make any accommodation necessary to insure my health and well being. I hope you find a good solution. Safe travels!

Ever since I had to endure a hard as rock pillow for several nights in Venice I have been traveling with my pillow. I put it in my suitcase last and it kinda flattens down over everything. I feel like it holds everything in place. It is down and I do use a larger suitcase (25in) because I always check my bag but I think I’d rather use a larger bag than keep track of a separate bag for the pillow. I also always use a unique or at least non-white pillow case so I can easily spot it as I'm packing to check-out so I don’t leave it behind.

My cousin travels with us and brings her specialized Full body pillow. She shoves it in one side of her suitcase and when she opens it, i am always amazed she got that thing in there. One time she put it in a carry on and checked her regular suitcase. She said she can replace everything else overseas but not her pillow. You’ll figure it out.

Not a pillow, but I have had good luck stuffing my down jacket in a 2-gallon Ziploc bag, zipping it most of the way closed and then sitting on it to compress the air out and zipping the rest of the way. No vacuum required.

I can highly recommend this website for quality made travel pillows. The perfect travel pillow for all your journeys. Many beautiful designs to match your style of travel. Great customer service. Also great for gifts as well. The pillow fits well into a personal carryon bag.
https://www.etsy.com/shop/campincomfort

I travel with a 25 inch suitcase and always pack my pillow. It is the last thing that goes in my bag and compresses easily when I lean on the top while I zip it.

Hey, you can handle a pillow.

Three years ago, I carried all my stuff in a backpack suitcase, towed my wife's 21" TravelPro carry on bag and pushed her in a lightweight travel wheelchair. And not once did I get any porter to help us anywhere in 4 countries. She since had her knee replaced.

We're leaving for Berlin 10/1/2021, and my wife is recuperating from a mid foot fusion. This time, she's got an electric scooter that runs 7 mph and has a 10+ mile range. My problem is trying to keep up with her in the museums.

When you have a will, there's a way.

Wow David you amaze me!

Success on this front! I did two things: one, I did buy a small “Slip-on” bag that will slip over the handles on my roller bag; two, I bought the Amazon Basics vacuum bags which come with a hand pump. Just practiced sealing the pillow with the device and will allow me to put the pillow right on top of the roller bag. I will take an extra bag and the little hand pump that came with it which is about the size of an umbrella. Also whoever suggested the tip of taking a non-white pillowcase so you don’t forget the pillow, great idea.

Anyway thanks for all the support and tips. Super glad it will fit on top so I can get everything packed and then just put this in at the last minute. Would’ve not liked having to pack the whole roller bag at the last minute as I am normally an early bird.