---
source_url: "https://frequentmiler.com/ways-i-self-insure-my-trips-with-strategic-booking-and-credit-card-choices/"
title: "Ways I \"self-insure\" my trips (with strategic booking and credit card choices)"
mirrored_at: 2026-08-15T01:38:25.371Z
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mirror_canonical: "https://index.42a.ai/frequentmiler.com/ways-i-self-insure-my-trips-with-strategic-booking-and-credit-card-choices/index"
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> **Original source:** https://frequentmiler.com/ways-i-self-insure-my-trips-with-strategic-booking-and-credit-card-choices/

Several times a year, we field reader questions about travel insurance. Unfortunately, I don’t have a lot of insight into travel insurance because I never buy it. **That’s not to say that you shouldn’t buy travel insurance**. I put that in bold to make sure you didn’t miss it; this post is _not_ meant to discourage you from buying travel insurance if you decide that it makes sense for you. Many people buy travel insurance and I’m sure you won’t have to wait long for a comment to come in about why someone was grateful they had it. This post isn’t to tell you _not_ to buy travel insurance. If I were going to consider buying travel insurance, it would be to cover against medical emergencies. I’m _not_ concerned with buying travel insurance to cover “travel” emergencies. Instead, I self-insure against those with habits I’ve picked up from this miles and points hobby.

![](https://frequentmiler.com/wp-content/uploads/2024/08/Airport-flights-cancelled.jpg)

In this article:

-   [Book using a card with trip delay / cancellation / baggage protection](#Book_using_a_card_with_trip_delay_cancellation_baggage_protection)
-   [Book easily refundable awards](#Book_easily_refundable_awards)
-   [Book flexible rates](#Book_flexible_rates)
    -   [Hotels](#Hotels)
    -   [Car rentals](#Car_rentals)
    -   [Tours](#Tours)
-   [Book backup flights](#Book_backup_flights)
-   [What about medical events?](#What_about_medical_events)
-   [Bottom line](#Bottom_line)

## Book using a card with trip delay / cancellation / baggage protection

![a hand holding a cell phone and a credit card](https://frequentmiler.com/wp-content/uploads/2021/06/Credit-Cards-and-Google-Flights.jpg)

I always book my trips using a credit card that offers coverage against trip delay or cancellation and baggage protection. **All** of my flights go on a card that offers this coverage.

We have a [complete guide to ultra-premium credit card travel protections,](https://frequentmiler.com/ultra-premium-credit-card-travel-insurance/) where you can compare the offerings from various cards. However, my clear favorite of the bunch is the coverage that comes standard on the [Chase Sapphire Reserve](https://frequentmiler.com/csr/) or [Chase Ritz-Carlton Visa Infinite](https://frequentmiler.com/ritz/). All of my flights go on one of those two cards, **including award flights**. That’s because trip delay & cancellation protection kicks in on those cards when you pay **any part** of the fare with your card. This means that using your Sapphire Reserve or Ritz card to pay the taxes & fees for an award ticket, even in cases where those taxes and fees are just $5.60, activates trip delay and cancellation coverage (as well as lost luggage reimbursement, etc).

In all of my travels, I’ve only had occasion to actually need trip delay coverage once, but the night when I got delayed overnight and got stuck paying for a hotel that cost more than $400, I was certainly glad to have the peace of mind that I’d get reimbursed thanks to the trip delay coverage I had gotten by putting the taxes on the right card.

It’s worth mentioning that I never use an airline credit card to buy my ticket. I keep some airline credit cards for free checked bags, but we can earn 3 transferable points per dollar spent using the Sapphire Reserve and we get excellent travel protections when using that card, so in most cases it just doesn’t make sense to use the airline credit card for an airline purchase. Note that you _do not_ need to buy your ticket with your airline credit card in order to get free checked bags from your airline credit card (if your card offers that benefit) unless it is a United card (unlike other airline credit cards that offer a free checked baggage benefit, United does require that you use your United card to pay for the flight and/or award taxes). See our [Free checked bags via credit card complete guide](https://frequentmiler.com/free-checked-bags-via-credit-card-complete-guide/) for more detail.

If your trip gets cancelled for a covered reason, the Sapphire Reserve or Ritz card cover you for up to $10,000 per person / $20,000 per trip in nonrefundable travel expenses. Luckily, I haven’t yet had to make such a claim, but I’ve heard from readers who have had approved claims in the five figures.

## Book easily refundable awards

Most of the flight bookings I make are easily refundable, either for free or quite cheaply.

Great award pricing is of utmost importance to me, but I also keep a keen eye toward those programs  which offer free or cheap award cancellations whenever practical. I’m not willing to significantly overpay for an award to have a cheaper cancellation policy, but there are a number of programs with award cancellation fees of $100 or less.

See a full [guide to award ticket change and cancellation fees by transfer partner in this post](https://frequentmiler.com/award-ticket-change-and-cancellation-fees-by-transfer-partner/). Some of my favorite programs for free or cheap cancellation are:

-   American Airlines AAdvantage (free changes and cancellations)
-   Southwest Rapid Rewards (free cancellations)
-   United Mileage Plus (free cancellations)
-   British Airways Executive Club ($55 or just forfeit the taxes if the taxes & fees are less)
-   Virgin Atlantic Flying Club ($50 or just forfeit the taxes if the taxes & fees are less)
-   Air France / KLM Flying Blue ($70 chance or cancellation fee)
-   Avianca LifeMiles (free changes and cancellations with LifeMiles+ Basic subscription or higher)

Note that the above isn’t an exhaustive list but rather some of my favorite award booking programs from an award change & cancellation standpoint. See the post linked above for full details.

I love that LifeMiles now offers free award cancellation (72hrs in advance or more) with a monthly subscription to LifeMiles+ Basic or higher. LifeMiles has historically offered some great award pricing, but particularly punitive change and cancellation fees. Since the launch of the LifeMiles+ subscriptions, things have improved. If you’re willing to subscribe to LifeMiles+ Basic or higher, the program feels much more user-friendly.

In addition to booking freely or cheaply refundable tickets, I also tend to book one-way award tickets in either direction instead of a round trip. My rationale is that I want to be able to change one side of the trip without messing with the other. If my flight gets significantly delayed or cancelled on the outbound, I want the freedom to book something completely different (perhaps on a different airline/alliance) to get me where I need to be without jeopardizing my “return” leg. If, for instance, my “outbound” flight gets delayed for hours, I can easily cancel it and book something entirely different without losing my desired “return” leg so long as I’ve booked separate one-way awards.

The “Crowdstrike” event of 2024 is a prime example of why I’d rather have separate one-way trips: if my outbound flight got cancelled in that debacle, I’d like to be able to immediately book whatever replacement I want rather than being limited to what the operating airline can do to accommodate me and/or trying to figure out what might be reimbursed by my travel insurance.

Many airline programs offer free cancellation or low cancellation fees like $25-$75 per passenger. If I can get my miles back for a nominal fee, I’m not concerned about insuring against paying those amounts.

## Book flexible rates

### Hotels

In the past decade, I’ve probably only made 3 or 4 nonrefundable hotel bookings. Generally speaking, I have no interest in locking myself into a booking with no way to cancel if my plans change or if I find a better way to stack a deal. While prepaid rates sometimes offer modest savings over refundable rates, I often find that AAA rates are refundable and approximately match (or sometimes beat!) a hotel’s nonrefundable rates.

I also like to maintain flexibility. Plans may change unexpectedly, but I also want the ability to jump on a better deal if I find one. For instance, if a shopping portal suddenly offers a high percentage back or a sale drops the price at an even nicer hotel to be significantly better, I want to be in a position to take advantage of the better deal. I have many times rebooked a hotel when rates have changed and ended up saving far more than the original “nonrefundable” rate.

I highly value hotel award bookings because most hotel award bookings can be cancelled for free up until a day or two before arrival (with some exceptions; always read your hotel’s cancellation policy carefully before making your booking).

Speaking of the cancellation policy, keep in mind that you may have even more flexibility than you think. For instance, Hyatt Globalists get a 24-hour cancellation window even when the hotel’s cancellation policy for the general public says 48-hours (though if the hotel has a cancellation policy of more than 48 hours, you’ll be held to that publicly-stated policy). I have also sometimes found it possible to _change_ a hotel reservation even after the cancellation deadline has passed. For instance, I had a reservation for a hotel with a 48-hour cancellation window, but at the 24-hour mark (prior to check-in), I was able to _change_ the reservation to be for a date a few months in the future. Then, I could cancel any time before the new deadline. In cases where I haven’t been able to do that online, I’ve sometimes had luck calling the hotel front desk and pleading my case.

Again, I use the Sapphire Reserve or the Ritz card to pay for the rare prepaid hotel booking so that I have trip cancellation insurance in the event that we need to cancel.

### Car rentals

Most car rentals can easily be cancelled for free up until the time of pick up (and some can even be cancelled later than that).

You can sometimes score a small discount by prepaying for a car. However, I don’t usually do that. Instead, I book a flexible rate and then use rental car comparison site Autoslash.com to track rental prices. I then cancel and rebook repeatedly as prices change, which might not be possible with a “pay now” rate.

I did recently pay in advance for a reservation I made through Autoslash with a “Pay now” discount. In that case, I paid using my U.S. Bank Altitude Reserve. That card also features very good trip delay and cancellation coverage and it also offers a chance to use points toward paid travel at a rate of 1.5c per point when redeeming via Real-time mobile rewards.

One additional thing that the Altitude Reserve shares with the Chase Sapphire Reserve, the Ritz-Carlton Visa Infinite, and several other travel cards on the market is that they all offer **primary** rental car collision damage waiver (CDW). That feature covers damage to the car in the event of an accident. Our own [Stephen Pepper had to make a claim several years ago for a rental car damaged in a hail storm](https://frequentmiler.com/my-experience-using-chase-sapphire-reserve-rental-car-insurance/). I always rent a car with a credit card that features primary CDW coverage.

### Tours

I rarely book tours, preferring instead mostly self-guided travel. However, in recent years, I have on occasion booked prepaid tours. In those cases where I have booked in advance, I’ve used popular sites like Viator and Klook, which have offered free cancellation up to 24 hours in advance for most of the things I’ve booked.

Much like hotels, I would be pretty hesitant to book a completely nonrefundable tour. That said, if I were in a situation that required it, I would likely book with the Chase Sapphire Reserve or Ritz-Carlton card for excellent trip cancellation coverage.

## Book backup flights

When I really need to get somewhere and can’t afford a misstep, I occasionally book a backup flight using one of the many programs with free award cancellation.

For instance, if I need a positioning flight for an important international award or I need to arrive on a specific day for a meeting or event, I’ll often book a backup secondary flight with American Airlines AAdvantage, United Mileage Plus, or Southwest Rapid Rewards. That way, if my primary flight takes off as scheduled, my trip won’t be ruined.

I don’t _always_ book a backup flight, but when it’s important that I get somewhere on a specific day or time, I tend to ensure that I’ll get there by making sure that my “Plan B” is covered _before_ a disruption occurs. In those cases, I usually set a reminder to cancel as soon as I know that my primary plan has gone forward without issue. One time, when I had not booked a backup flight but arrived at the airport and saw an unbelievably long line for airport security, I immediately got on my phone and booked a backup flight knowing that many of the people in line were likely to miss their flights and need to rebook. When I got up to the TSA agent, I had already missed my first flight, but I had the boarding pass already for the second flight I’d booked and I therefore got to skip the long line of passengers waiting to be reaccommodated on my initial airline.

Note that you probably can not book your “backup” flight with the same program through which you’ve booked your “primary” plans. If an airline sees two bookings for the same passenger on the same day and it is impossible to make both flights, they may cancel either or both of the bookings. I therefore use a different program / airline for my backup plans.

## What about medical events?

While my booking habits mostly make it easy enough and/or cheap enough to cancel plans when necessary, the big question mark is what happens in the case of a medical emergency.

That’s a great question that I can only partially answer. I think that coverage for medical emergencies is the most important reason why a credit card rewards enthusiast might still consider buying some type of travel insurance. In the couple of cases where I bought travel insurance, a potential medical emergency was the core reason for buying insurance.

On the one hand, medical costs outside of the United States can be very reasonable in many (most?) scenarios). My wife got double ear infections in South Africa on a trip 8 or 9 years ago. The emergency room bill, which included the visit itself and the medicine they gave her, came to about $105. I had paid our award taxes with a card that included some emergency medical coverage, but I never bothered making a claim.

On the other hand, I’ve heard from readers who have encountered horrific accidents that required extensive (and expensive) medical treatment. There are plenty of worst-case scenarios to imagine. If I were shopping for travel insurance, medical coverage would be the single most important component for me.

That said, there are some medical coverages provided by popular cards. In our [guide to ultra-premium credit card travel protections](https://frequentmiler.com/ultra-premium-credit-card-travel-insurance/#Emergency_Medical_and_Dental), you’ll see that the Chase Sapphire Reserve and Ritz cards offer up to $2500 in emergency medical and dental coverage. Additionally, the American Express Platinum Card® and Centurion card holders get emergency medical evacuation coverage, with no requirement to have used the card to pay for any part of the trip. A friend had to make use of this benefit while on a cruise a couple of years ago and was flown back to the United States with Amex covering the full $27,000+ bill. I will note that they reported having to advocate a bit for the medical necessity, but Amex approved it with minimal pushback. It’s worth noting that many readers have commented about how Amex’s coverage only guarantees transportation to “a more appropriate medical facility or to a hospital near the person’s home as determined by the Premium Global Assist Hotline designated physician”, whereas travel insurance policies specializing in medical evacuation can be purchased to guarantee transportation to the hospital of your choice.

At the end of the day, emergency medical coverage isn’t well-provided by credit card benefits and is the primary reason I think it could be worth buying insurance.

## **Bottom line**

Readers often ask us for travel insurance recommendations, but the truth is that I have rarely bought it. If I did buy travel insurance, it would be for medical coverage because I look to my credit card and booking habit strategies as a means of insuring myself against travel-related problems. Credit cards definitely leave a gap on the medical side, but I don’t worry much about travel plans changing since I know that I can afford to cancel a trip if necessary.

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