I have been putting most of my airline/travel spending onto my Chase Sapphire card. Not just for the points but also for the insurance. I have successfully claimed the lost item insurance before but have not attempted the flight delay insurance.
The Chase Sapphire Preferred card covers expenses up to a maximum of $500 when a trip is delayed by more than 12 hours.
Now the HuffingtonPost is running a real-life case (at least it sounds like one):
Knowing that he has the trip-delay reimbursement at his disposal, Anthony made a note to keep receipts for all expenditures during the delay. In total, he spent $450 for his hotel stay, cab rides, meals and bar tab.
Upon return from the trip, he immediately called to file a claim, which is actually handled by Visa. Soon after providing a brief description of his case, he received an emailed claim form to fill out (which he received while still on the phone with Visa).
Then, he called US Airways for a statement explaining the cause of the trip delay — a two-sentence email was sent to him that same day. This is required to file a claim.
In an manilla envelope, he mailed:
Copies of receipts for claimed expenses
A copy of his US Airways ticket
The printed statement via email from US Airways
The claim forms
Eventually Chase came through and reimbursed the claimant in full. However, it easily takes 2-3 hours of work, if not more. Also 12 hours is REALLY long – I have had a lot of cancelled flights lately but usually end up with 3-6 hours as the airlines have been trying to rebook me. Still, it's a great benefit to have!