The answer to this question involves investigating a number of parables not explicitly stated in your question.
20 Moreover, pray that [p]when you flee, it will not be in the winter, or on a Sabbath
But when it comes to his predictions concerning the destruction of Jerusalem and the flight of Jews Christ is not specific.Christ makes mention of whether it will be on a winter or on the Sabbath,but without giving a specific time.
If one reads the Maccabees, you'll find that "Your flight not be in winter" is a reference to Hanukkah, for which Maccabees is the basis. He is not necessarily stating that it will happen on Hanukkah. It's essentially a trigger to remember the details of the Maccabean revolt. Jesus spoke many things in parables, and often responded to a question in a parable - i.e., he would provide you a way to find the answer without stating it explicitly. Jewish reasoning is circular, not linear - i.e., what happened once will happen again. Perhaps not exactly, but it will be pretty close.
Consider that the destruction of the first and second temple occurred on the same day (9th of Av) - and how what happens once will happen again. Maccabean revolt lasted 7 years. There was also an abomination of desolation. Perhaps this 7 year period (tribulation) will also repeat on the same day and in a similar manner.
Did Christ not know the specific season and day when this will take place?
Matthew 24:36 says: But of that day and hour know no man, no, not the angels of heaven, but my Father only. Since Christ is on earth is fully man, he is not going to know the day or the hour but he does expect us to have a very good idea of when. God's calendar that he gave us are appointments (the 7 feasts) that he expects us to know. Knowing what the feasts are and what they represent are key. The 7 feasts require us to observe the moon to know when it starts. At the end of days, the sun and moon will be darkened as stated in Matthew 13:24, Matthew 24:29, Joel 2:10, Joel 3:15, and Revelation 6:12. Henceforth, no one will be able to determine when the feasts (appointments) will start. Jesus the man won't know exactly, but the creator - Jesus as God - will.