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With the recent flight cancellations, it seems flight insurance is necessary if I fly Southwest. Southwest will not place passengers on other airlines. It seems smarter to book Southwest and if the flight is cancelled use the insurance company to be booked on another airline.
Does anyone have recommendations for flight insurance?
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Other reports about obtaining typical travel insurance with a Southwest flight have mentioned the insurance provider is not willing to pay out since you still retain the value of your purchase as travel funds if you cancel your flight and if Southwest cancels it you get a refund back to your original form of payment. Perhaps if you had trip disruption coverage which is offered for free on many credit cards your concern would be covered
Overall, your odds are still rather minimal so thinking you need insurance for every flight because Southwest is cancelling every flight is blowing it way out of proportion.
--TheMiddleSeat