My pillow solution for my BOB, camping, travel, etc, is the Eagle Creek inflating travel pillow that is basically a horseshoe that goes around the neck. It keeps your head from flopping around when trying to catch a nap while sitting upright (car passenger, airplaine), and only weighs a few ounces when deflated. Two good breaths and it's blown up. For field use I find it keeps my head up and in a comfortable position for sleeping, and stays with me if I roll around, which rolled up jackets and extra clothes usually don't. I think they're still about ten dollars at REI, EMS, etc, or there's the cheaper versions available. They pack into about three cubic inches and should fit in your BOB without any problems.