If it’s doable then I make a point of offering a late checkout the night before, I just say, “you guys are welcome to check out later, sometime in the afternoon if it works with your schedule”. I only offer a late checkout if I don’t have a same day check-in so it doesn’t matter how late they checkout once I offer it so I don’t give a time limit, though some do ask, “is 2 okay?” or something. And as @CatskillsGrrl 's guests, most of mine need to leave earlier anyway. But some of them have a 4pm flight and are ectastic to stay until 1 or 2.
I certainly don’t mind someone asking but I get really steamed up about guests who dawdle for an extra 15 or 20+ minutes without asking or being invited to do so. So different strokes I guess.