Q.  Dear Rabbi
What is Horav Miller’s opinion in regards to someone who had a repeated dream that he should not travel to a mishpacha simcha in Israel, because it will end in a tragedy, Can he go? Does he do hatavas chaloim?

A. Much has been written to explain the value of dreams in our tradition as there seems to be a degree of unclaraaaaity and ambiguity in the words of our Sages as to the worth of dreams. On the one hand, the Talmud states that dreams are one-sixtieth of prophecy (Berachos 57b), and a dream which is not interpreted is akin to an unread letter (55a). Yet at the same time the Talmud writes that no dreams are without nonsense (ibid., 55a), “Just as wheat cannot be without straw, so there cannot be a dream without some nonsense,” and one’s dreams are merely a reflection of what one is thinking during the day.. The interpretation of a dream depends on the explanation given by the interpreter (55b). As the Talmud makes clear, any dream can have either a good or a bad interpretation, and he may be at the mercy of the one who interprets it.
Shulchan Aruch (O.H. 220: 1- 2) describes the hatovas chalom ritual a person should follow when he experiences a dream that stresses and perturbs him, also the importance of the fasting, even on Shabbos to mend and rectify the dream. The above, should be done the same day and be accompanied with teshuva (Mishna Berura ibid. 6).
However, Shulchan Aruch (C. M. 255: 9) also rules that if a security was given to the now deceased father and the son does not know if his father received it or where he placed it. If he is then informed in a dream (Tur explains; even by the father himself), where the money is to be found, the amount and to whom it belongs. And behold, he actually finds that correct amount of money at that same place, he can keep the money for himself, since the words of dreams do not make a difference. (The S’ma, ibid. 29, explains that the part of the dream informing to whom it belongs, may not be true).
Tashbatz (2: 128) elucidates that dreams, their meaning and validity is a complex issue and depend on many different factors around and about them, such as who had the dream, who was the informer of the dream, etc. Orchois Tzadikim (Shaar Haemes) maintains that a person trained and disciplined in telling and thinking only the truth, will experience similar dreams. In general, Tashbatz writes, that some vivid or repetitive dreams can create a situation of doubt as to their veracity, and one should treat them as such. Therefore, when they involve a monetary issue, as a rule possession trumps and the monies or obligations stay where they are. However, Emek Shaila (Miketz, Sheilta 29: 15) adds, that following his ruling, when dealing with prohibitions (or mitzvos) such as if one dreamed, that a certain food (of his) is not kosher (on a Biblical level), he should treat it as a doubtful Biblical prohibition and it remains forbidden.
Horav Shlomo Miller’s Shlit’a opinion is that in your case, since it involves a mitzva of traveling to Eretz Yisroel and partaking in someones simcha, you should follow the rule of the Shulchan Oruch (O.H. 220) quoted above. The Rov recommends to do hatovas chalom and give tzedaka as pidyon nefesh. (redemption of the soul).

Rabbi A. Bartfeld as revised by Horav Shlomo Miller Shlit’a