Absolutely, never want to be separated from the meds but I am sure she knows that. She will also take a cross body purse. I suppose these things will fit there.

Since you have the ebags weekender I can give you the very strong recommendation to have the backpack straps stowed away when arriving for check-in AND at the gate. Backpack straps are a red flag and it is much more likely for them to demand to get the bag checked if they see them. Seriously!

Till

I have traveled for five weeks with two pairs of slacks, a dress and a pair of shorts and my running clothes, plus t shirts and a couple of nicer Ts (and underwear and pjs). One does not need five pairs of slacks for five days.

Oh, and I'm a ziplock fan. I put dress Ts in one bag, grungy Ts in another, underwear in one, running clothes in one. I don't have to dig around in my bag looking for my clothes. Now, if I'm going to be in one place and I'll unpack for the week, I'll skip the zip locks.

Don't be "too" efficient outbound
 

Great overview. I've been blown up by packing methods that are "too efficient" outbound. They leave no room for souvenirs on the way home. Not even room for "hasty packing." I swear a few times I've wondered how I fit everything in, outbound, when it comes time to pack for the return flight.

I also used to disdain packing cubes. But, now I like them because it's more efficient to locate the right cube, then pull out next day's clothes, than go through the entire bag. Hence, tee shirts cube, underwear and socks cube, casual shirts cube. My spare pants don't need a cube because they are so few in number (one jeans, one travel fabric) and so obvious.