I have a friend that frequently gets into ORD, recently during the middle of a day (saturday) but its in a seneca. These are my 2 thoughts

1. He catches them at the right time
2. The plane is a high use rental and is frequently buzzing all around CHI airspace, so controllers may get use to this call sign. However I feel it would be tough for them to remember the call sign with the volume of traffic at ORD. I just think its a local twin, and the controllers don't mind accommodating.