Trip Insurance: When Does it Matter?

Over the weekend, my younger brother was returning to college located in Milwaukee. Flying out of SFO, we seldom experience weather delays, and weather related cancellations are a rarity. Well, last weekend, freezing temperatures and an ice storm led to Southwest cancelling my brother’s flight. As a result, my family and I scrambled to re-book with United. As a frequent traveler, I have the American Express Platinum Card and the Chase Sapphire Preferred, both of which come with Trip Insurance as of 2020. Since my brother did not have a travel credit card, my parents tacked on trip insurance for an extra $10.

My brother’s flight was delayed for almost 10 hours due to a snow storm in the Midwest. Since there are no direct flights from SFO to Milwaukee, my brother had to transfer in Chicago resulting in the second segment being cancelled. The trip insurance I purchased came in handy for covering the cost of food for the day as well as the brother’s on night hotel stay by O’Hare Airport. The insurance policy covered cancellation and prolonged delays, allocating up to $500 a day for room and another $100 per day for food.

With such turbulent weather, hotel rates skyrocketed in a span of 15 hours with rooms at the Hilton Chicago Airport going from around $180 a night to over $400 a night. I was able to book a single night at that rate for my brother using my Hilton honors accounts by calling in and working with a wonderful representative. When attempting to make a last minute booking for a family or friend, I strongly suggest trying to use the Hilton service line. I was even able to earn 8500 Hilton honors points from this stay plus an additional 5000 points as I paid with my American Express Hilton Honors Card.


I was never a true believe of purchasing trip insurance, but this has gone a long way to change my mind. While I am covered with the American Express Platinum Card, I am definitely appreciative of trip insurance and will ensure my family is always covered when traveling. While this is the first time I have used insurance, I was surprised at the simplicity of the claim process. I believe trip insurance should be an essential for any large trips.

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