Oh - now that one I have totally figured out!! I have a
massive rolling duffle bag, that gets both of our clothes, etc. Then I have a rolling backpack for the plane, that gets medicines, the travel DVD player, snacks, etc. (the key here is that it's a rolling
backpack - more on that in a sec) My daughter has her own little rolling Tinkerbell suitcase that gets her toys for the plane.
To get to/from the car, I roll the big suitcase and wear the rolling backpack on my back with the backpack straps. My daughter rolls her bag (has managed this since she was 3
). That leaves us each with 1 hand free, so I can hold her hand to make sure she doesn't get lost. If I end up with another suitcase somehow, it just gets attached to the rolling duffle via those strap thingys, although it makes the whole process more awkward so I really try to keep to the one suitcase if possible. Once the suitcases are checked in, I can take the backpack off my back and roll it through the airport, which is way more comfortable!