Depending on the type of tiller and the size and density of the rocks your experiences will vary. I've tilled relatively rocky soil using a huge rental tiller that had a sophisticated hydraulic drive system and it did a fair job but still left me to manually pick up and dispose of the rocks.
Far easier and quicker is to find a local company with a Bobcat-type machine that has a rock-picker attachment. They can readily pick out everything over about 3/4" leaving decently clean soil for you to amend and work with. It is amazing how much an experienced person can do with a Bobcat in a couple of hours and the cost is probably less than you imagine. It certainly can't hurt to ask. BTW: there are also huge tiller attachments to go with the Bobcat and the machine with a bucket on it can rip up really bad tree roots and such with almost no fuss.