I don't travel often, and fly less, but this is an issue every time and I want to work on a solution. I recently flew with a wheeled carry-on, a cloth tote bag, and my purse. The tote bag held another cloth bag with my iPad and Kindle, glasses, and snacks. My purse held what it normally does.

My gaming the system when boarding was to put my purse into the tote bag also. I had done this before but there is surely a better solution. It was super heavy and bulky, and awkward too because the tote bag didn't close so things tipped over once and I almost lost my keys.

I can think of two solutions. Find a tote bag that functions as a purse...internal wallet structure built in and pockets for phone and keys...plus room for the extras like the iPad/Kindle/snacks. Pack a smaller purse in the carry-on for use at destination.

Or...still do my two condensed into one but find a better tote, able to be zipped close, and find a smaller purse with the built in wallet pockets, etc, to take down the bulk and weight of a separate wallet.

Both solutions involve buying new bags, so I don't care which. Frequent travelers, what do you do? My main thing is that the tote can't be leather. It needs to be as lightweight as possible...good canvas or nylon. General advice is great, extra points for specific products.