How can I trigger messages based on a custome DATE Field

We have a Hotel, and use Kommo for whatsapp messaging and other platforms - When we add contact, we add their desired DATE of CHECK IN and CHECK OUT - We would love to be able to trigger message based on the date - See examples below

1- Send a message with check in instructions X amount of dates before the set date in the custom field

2- Similarly, send a thankyou message 2 days after the check out date

We want to ideally trigger this messages based on the field