If a person is alone inside the home and trying to lift the suitcase through the window well and through the grate, then it seems to me it would be very difficult. If you were to put the suitcase on the ledge first, then you could not get onto the ledge with it. If you were to get up onto the ledge and then try to lift the suitcase from the floor then you would have a problem when you got the suitcase near you because the ledge is small. Actually it could be impossible. However, if there were two people, one inside and one outside, it might be possible. What are the actual dimensions of the well?