Dear Mordechai,

Excellent question! Baruch Hash-m you are Mechaven to the view of the Tiferes Yakov!

1. The Tiferes Yakov understands that he was planning to redeem them, as opposed to simply helping them to flee. This would avert the prohibition of the Mishnah to which you astutely called attention.

2. The Maharsha, however, indicates that his plan was to help them escape by running away. In light of the difficulty you raised, this view could possibly be reconciled based on the Yosef Lekach (Yevamos 79a) who suggests that just as there is a Heter for oneself to run away, so too there may be permission to help one's relatives to escape. Accordingly, if we would assume that these women were relatives of Rav Ilish, consequently there would be no prohibition.

3. Possibly, if the situation was one in which there was a threat of death, then this would be subject to the dispute between Tosfos, who waives the law of our Mishnah in such a case, and the Ramban, who does not waive it.

I hope this helps!

Best wishes,

Yishai Rasowsky