I'm planning a trip by air and am worried about losing my checked suitcase. I need to check it because I'm packing walking poles and they are not allowed as carryon on my airline. I plan to have most of my checked bag empty and also take a soft-sided carryon and personal item. When I land at my destination, I want to be able to put my overhead carryon inside the checked bag (either complete or, more likely, take the packing cubes and put them in, and then lay the empty bag on top) and have just the wheeled checked bag and a small personal item to manage to get to the hotel.
I can put my tech stuff in the personal item. I'd like to put most of the clothes in the overhead carryon, using packing cubes. This way, if my checked bag is lost, I will still be okay. I have narrowed it down to Patagonia 40 Liter duffel with backpack straps or the Rick Steves Classic Bag. I think I can pack more efficiently in the RS bag, but will it collapse a bit and be somewhat flexible to fit into a checked bag of approximately 28" x 14" x 10"? How floppy is it when empty? Could you fold it in half when empty? Thanks!