Can a person with winged boots carry another medium size creature, and if so, would it require any checks?
I found this info in the DMG, page 214:
Wondrous item, uncommon (requires attunement
While you wear these boots, you have a flying speed equal to your walking speed. You can use the boots to fly for up to 4 hours, all at once or in several shorter flights, each one using a minimum of 1 minute from the duration. If you are flying when the duration expires, you descend at a rate of 30 feet per round until you land.
The boots regain 2 hours of flying capability for every 12 hours they aren't in use.