Mine just go outside quickly

We clear a large spot for them in the yard if the snow gets too high. I think they have a harder time with the transition to cold than the cold itself. At first we put tanks and sweaters on them but by January they just run out there naked. If they are just peeing for 30 seconds it's fine. Have you ever run out to get the mail in the cold without a jacket? Same thing.
I have coats for them and the coats are good for when they are going to be outside for a few minutes or more, to play in the snow or take a short walk. It's more of a hassle than it's worth to put them on for quick trips out so we try to just leave hoodies on them during the day and those are fine for potty breaks. Mine do fine in the snow, they dislike the wind and the rain. If they refuse to go out I just stand on the porch with them and they realize they aren't getting back in until they go so they hurry it up
Really, Loki will be 4 this month and Sammy is 2 and we live in Chicago. It's totally doable.