As the above poster I can only speak t my own personal experience.....I did have more severe headaches when I would get my monthly...and it is a lot of swelling and inflammation that occurs with that and with swelling comes tighter space for blood and CSF to flow which with Chiari is tight already.....
Deff talk with your OBGYN and NS to see the best way to deal with this.....not knowing your age....there are things I wish I knew when I was younger as I went into early onset menopause....I also have Hashimoto's thyroiditis and that can affect hormones and in effect affect headaches too.
Talk with your Drs to get the proper guidance for you.
I can only tell you about my experience. I did have severe headaches the week before, during & after my menstration cycle, however I was never sent for MRI therefore was not diagnosed with Chiari at the time. My OB gave me Imetrex pills & Estrogen patches which did help immensely.
I think the headaches really were hormone related at that time. I have since had a complete hysterectomy, so I no longer have that issue. I do remember the headaches were so severe it was debilitating at times. I would suggest getting hormone levels checked. It was noted that my Estrogen level dropped significantly during my cycle. Good luck & hope you get relief soon!!