Away The Bigger Carry-On, $245
I usually swear by the Allpa 35L ($200) from Cotopaxi (it's far superior to other iterations I've tried), but I wanted something more traditional on hand for this trip. I got the Away Bigger Carry-On ($245), and I was viscerally grateful for it at just about every step of the way.
The shell is tough but flexible, and the two internal compartments make packing easier — one side for clothes, one for hard objects like shoes and toiletries — and you can fit a surprising amount (I had quite a few spare outfits for a five-day trip). The 360-degree rotating wheels made it a breeze to roll the case along one-handed and without exerting much effort. The external battery,which can charge any phone up to 5x, helped me at the airport, on the airplane (which, surprise, didn't have outlets), and throughout the trip as my go-to battery pack. The internal nylon laundry bag helped me separate dirty clothes from clean, and it made unpacking easier once I got home.
The suitcase also comes with a pack of adapters for charging the battery, and I used that throughout the trip as well as a spare.
$245 is more than I'd normally spend on a carry-on, but the convenience is worth it.