I try to avoid having to use rolling luggage when flying during overnight trips.
This Gucci messenger (above) housed three pairs of pants, three shirts, three hats, a bathing suit, a pajama set, underwear, socks and toiletries during my less-than 18 hour visit to LA last Saturday. It worked because all of the items revolved upon use. I was always wearing one of the three outfits while the other two remained packed.
Every item seemed to be small enough to fit into the bag with consistent organization. I never felt like I didn’t have enough options because everything included was well thought out and planned. It was really nice for me (and my driver) to not have to deal with carrying or checking in any luggage at the airport.
All I’m saying is, you shouldn’t have to lug a ridiculously huge rolling trunk around just for an overnight trip.
Efficiency is key.