I thought I'd share my recent experience using the trip cancellation insurance on my Chase Sapphire Preferred card. I had booked a September trip to New Orleans for our anniversary, and my husband ended up having a spinal fusion in early August, so of course he wasn't quite ready to travel seven weeks later. I had used travel credits on United, which they graciously refunded, but I had booked a non-refundable hotel room through Expedia, who did NOT graciously refund me. I used Chase's online portal to upload my documents (doctor's note, hospital notes, hotel receipt, flight cancellation), and while it took a little while (okay, almost two months), I just received notification that they would be crediting my card for the full amount of the room. It was a pretty easy process from start to finish.
The best part is that I've convinced my husband that since we missed our anniversary trip, we should just go to Ireland instead :D