We had to cancel a trip to Greece and The Netherlands scheduled for my husband, daughter, and myself from June 14 to July 5 due to some health issues. Overall, our claim with Chase Sapphire went well and money was in our bank account within 9 days of submitting the claim. See below for more details if you are interested.
We had paid for all expenses with my husband's Chase Sapphire Preferred Card, so we used the insurance to cover our penalty charges for Sky Express flights round trip Athens to Naxos & one-way Athens to Amsterdam, and for our first hotel. Most other charges could be cancelled without penalty.
The process was a bit of a pain. On the plus side, you can start a claim and save and return to it if you need to find more documents, which is very helpful. When you are ready, you click the button to submit. Once you submit, you can no longer see what you requested, so I recommend taking some screen shots or being sure to write down all details. I soon realized that the same document would satisfy a number of their categories that required document uploads (ie cancellation policy, amount refunded, penalties, itinerary, etc) but you need to save the document with a different title to post in each category. A bit of a pain, but fine once I figured it out.
I submitted on 6/19, heard that the claim was approved on 6/26, and the money was refunded on 6/28. Phew!