Several countries in Europe have had that for some time now – and finally Berkshire Hathaway launched it too – Trip Cancellation and Missed Connection Insurance!
It's priced at $25 and you can buy insurance up to 1 hour before the departure of your first flight!
If a flight in your itinerary is delayed beyond 2 hours, or you miss a connection, the insurance pays out:
If you miss a connection due to a flight delay, we'll instantly arrange transfer of $500 into your bank account.
If your departing or connecting flight is delayed by 2 hours or more, we'll transfer $50 to your bank account.
We'll automatically transfer $1,000 into your account if you sit on the tarmac for more than two hours.
There are no exclusions for award travel that I could find! You need to recreate your itinerary though on the website, so the company can make sure you are not using super-risky connections. International trips are covered for the same price if you can find your route.
The flight delay/ cancellation cannot be due to weather.
Here are more questions from the FAQ:
What are the time limits for buying travel protection from BHTP?
You can buy an AirCare policy up to one hour prior to departure. So suppose your flight is scheduled to depart at 3 p.m. Tuesday. The latest you would be able to buy an AirCare policy is 1:59 p.m. on Tuesday. There are a couple of caveats to that: The flight cannot already be affected in some way – cancelled or delayed because of weather, for instance – and the trip and travellers have to meet all eligibility requirements.
What are the eligibility requirements for AirCare?
For AirCare, the flight cannot already be affected in any way, the flight departure time must be at least one hour in the future, and all flight segments must be valid commercial airline flights (no hot-air balloons). Also, the customer, airline, airport, destination, and sales agent must not be on the government's blocked list; there must not be extreme weather taking place at the departure airport or destination at the time of scheduled travel; and the primary traveler must be 18 or older.
If my claim is approved, how will I be paid?
Your potential claims will be paid based on information you supply, to an account you specify. Payment options include check, EFT, or PayPal.
Is travel insurance expensive? Why should I have it?
We believe any trip is worth covering, and that's why we've created protection specifically for flights, as well as more comprehensive plans. AirCare starts at $25 and covers all the flights on your itinerary and all the risks and disappointments inherent in travel. With AirCare, instead of having to wait until the next available flight with your carrier you can arrange a new flight with any carrier to get you to your destination – which we all know is where you really want to be. AirCare is the one travel product we won't travel without. That and our charging cord; never forget the charger… We'd be happy to walk through our products with you. Quotes and pricing are available via our iOS and Android apps, via our website (BHTP.com), by emailing us at firstname.lastname@example.org, or by calling 844-411-BHTP.
Too bad insurance for CA residents is not (yet) available: