I have limited exp w/ this but here goes. If you are keeping rose cuttings in pots, they are going to be affected much more by cold and dryness than if they were in the ground (not to mention not having access to the minerals and bacteria that are in soil to sustain them). However, you are right that they probably won't survive the Chicago winter in the ground. I would try burying the pots (use terra cotta) -- put them in a sheltered place (like right up against a wall), and then either dig them into the ground a few inches or mound soil up around the bottoms.

Then *blanket* them, covering the pot completely all the way to the ground, and the ground itself, with a thick layer of grass clippings -- like 5 or 6 inches thick. You'd be surprised how warm this will keep them -- you can go out on a winter day and lift the grass and feel the soil in the pots, and it will be warm.

If you put the cuttings into the ground in the summer, so that they are established by the time the cold weather comes, you could also use styrofoam "rose cones" to protect them -- I've heard they work very well.

Thanks Chatwariq, Maybe I will try a few each way and see if one works better than the other. We work so hard to get these going only to have them perish in the winter is frustrating!! Would the terra cotta crack in the ground? I appreciate your advice.