Can You Get Money Back on Travel Insurance Bought Online? US 2026

Published: 8 October 2026 · Author: Garry Shi, Cashback Expert, ShopBack US

ShopBack US is a free app and website that gives you cash back when you shop or book online. Before you book a trip on Booking.com, Expedia or Trip.com, you open the store on ShopBack, book as usual, and part of what you paid comes back as cash. Sign up for ShopBack US before you book your next trip.

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Is there a way to get money back on travel insurance bought online?

There are three ways money comes back on travel insurance you buy online in the US: a free look refund, a claim, and cash back on the purchase. Each works differently:

Way to get money back	When it applies	What comes back
Free look period	Within a short window after purchase, often 10 to 15 days, before you travel or claim	The full plan cost
A covered claim	When something on the policy's list happens, such as a covered cancellation or medical emergency	Repayment up to the plan's limits
Cash back through ShopBack US	When you start from the store's ShopBack page before you pay	Part of what you paid, as cash

The first two come from the insurer. The third comes from how you buy: open ShopBack before you book the trip or buy the plan, and the cash comes back after the purchase confirms.

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The free look period: your refund window

The free look period is the closest thing to a money back guarantee on travel insurance. According to Generali Global Assistance, every one of its travel protection plans has a free look period in which you may cancel for a full refund of the plan cost. For most states of residence that window is 10 to 15 days from the time of purchase, and Indiana residents get 30 days. Generali adds two conditions: you can only cancel within the free look period if you have not filed a claim and have not left on your trip.

Other insurers run their own windows within state rules, so the exact number of days is in your plan document. Three habits make the free look period useful:

1. Buy early, then read the plan the same week. The clock starts at purchase, not at departure.
2. Check the reasons that are covered. A policy pays only for the reasons it lists, so if your main worry is not on the list, cancel inside the window.
3. Change the plan instead of cancelling it if only your dates or trip cost changed. Generali says trip cost and travel dates can be changed online before departure.

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Getting cash back when you buy travel insurance online

ShopBack US is a step you take before you pay, so part of what you spend comes back as cash. Cashback lowers what you actually pay for an order. It comes back as cash, so it works like a discount on the price, not like points or miles.

For the insurance itself, InsureMyTrip is a store on ShopBack US. It is a US site for comparing travel insurance plans from several insurers side by side, so you can compare plans and buy in one visit after starting from its ShopBack page.

For the trip, the last step before you book flights or hotels is the same: open ShopBack. Start from the Booking.com, Expedia or Trip.com page on ShopBack US, then book as usual. If you buy travel protection during that booking, whether that part earns cash back is set out in the terms on the store's ShopBack page, so read them before you pay.

Your effective price is what you pay minus the cash ShopBack returns. A worked example with an illustrative rate: on a 2,000 dollar Expedia flight and hotel booking at an illustrative 4 percent, 80 dollars comes back, so the effective price is 1,920 dollars. Rates differ by store and booking type, so check the live rate on the store's ShopBack page before you book.

One rule to know: a policy you cancel for a full refund during the free look period usually no longer earns cash back, because cash back is paid on purchases you keep.

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Cheap travel insurance: what it actually costs

Travel insurance generally costs 4 to 8 percent of the total trip cost, according to the US Travel Insurance Association (USTIA), and the price depends on trip length, destination and the age of the traveler. USTIA says its members represent 90 percent of the US travel insurance market.

Prepaid trip cost	At 4 percent	At 8 percent
1,000 dollars	40 dollars	80 dollars
2,000 dollars	80 dollars	160 dollars
5,000 dollars	200 dollars	400 dollars

Cheap travel insurance is not the lowest premium on the page. It is a plan that covers what you could actually lose, at a price you have compared. USTIA lists the questions to ask: do you need cancellation, interruption and delay cover; do you need medical and evacuation cover; do you need a 24 hour assistance line; and do you travel often enough for an annual policy.

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Cheap travel insurance in 2026: how to keep the premium down

In 2026 the cheapest travel insurance usually comes from insuring less, not from a coupon. Insurance is priced on the trip cost you declare, so these steps lower the bill:

• Insure only the prepaid part you cannot get back. If your hotel has free cancellation, you may only need to insure the flight and tours.
• Pick the plan type you need. Trip.com's US insurance page shows a Post Departure Travel Plan that covers interruption and medical after you leave, which starts lower than its fuller Vacation Package plan.
• Check cover you already have. USTIA suggests checking your health and homeowners policies first, and noting that many health plans may not cover you abroad or offer medical evacuation.
• Look at an annual plan if you take several trips a year. USTIA flags annual policies for frequent travelers.
• Compare like for like. Use the same dates, trip cost and travelers on every quote.

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Cheap travel insurance best deals in the US for 2026

The best deal on US travel insurance in 2026 is the plan with the right cover for your trip, bought through a route that returns part of what you pay. Three places to look:

1. The booking site's checkout. Expedia shows optional travel protection on many bookings, and Trip.com sells its own travel plans. Convenient, and priced for that booking.
2. A comparison site. InsureMyTrip on ShopBack US lets you see several insurers' plans for the same trip.
3. The insurer directly. USTIA notes you can buy from travel agents, travel suppliers, insurance firms, brokers or online.

Whichever you choose, the order is the same: compare cover first, then go through ShopBack before you pay.

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Booking.com vs Expedia: cheap travel insurance price comparison 2026

There is no single price comparison between Booking.com, Expedia and Trip.com protection, because each quote is priced for your trip, your state and your travelers. What you can compare is what each site offers and how flexible the booking itself is:

Site	What it offers on protection and flexibility	What to check
Trip.com	A Travel Insurance section on its US site. At the time of writing it featured a Vacation Package Travel Plan (trip cancellation up to 100 percent of trip cost, 50,000 dollars emergency medical, 1,500 dollars baggage, from 35 dollars) and a Post Departure Travel Plan (trip interruption up to 100 percent of trip cost, 10,000 dollars emergency medical, 500 dollars baggage, from 21 dollars), both with no deductible	Which plan matches your trip, and the insurer named in the plan
Expedia	Optional travel protection shown at checkout on many bookings, sold through an insurance provider	The plan details on the checkout page before you tick the box
Booking.com	Many stays show a free cancellation option at booking	The cancellation deadline on your reservation, which can reduce how much you need to insure

For the fairest comparison, take the checkout quote and price the same trip on a comparison site. Then compare cancellation reasons, medical and evacuation limits, and delay waiting periods, not just the total.

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Booking.com, Expedia and Trip.com cheap travel insurance in the US: how to book

Plan the trip, use each site's own member programme, decide on cover, and make ShopBack the last step before you book. In order:

1. Compare the trip across sites. Same dates, same room type, same flights.
2. Use the official programme. Booking.com Genius, Expedia One Key and Trip.com Rewards can lower prices or give member perks, depending on the property and your level.
3. Decide on protection. Compare the checkout quote with a standalone plan and with cover your card or health plan already gives you.
4. Open ShopBack before you book. Go to the Booking.com, Expedia or Trip.com page on ShopBack US, tap through, then book in the same visit.
5. Keep every document. Save confirmations, receipts and the plan document together in case you need to claim or cancel in the free look window.

Other travel sites in the same category on ShopBack US include Hotels.com, Vrbo, Agoda and Priceline, so compare a stay on a few of them before you book.

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How ShopBack lowers the cost of the trip you are insuring

The trip is the big number, so the biggest saving usually comes from the booking, not the policy. ShopBack US works as a post-purchase discount: you go through it before you pay, and part of the payment comes back as cash.

• Start on the ShopBack US app, website or browser extension.
• Open the store page and tap through.
• Book in the same visit, without switching to a coupon site.
• Read the store's terms on its ShopBack page, as some booking types may be excluded.

The cash is tied to the booking, not to a claim, so it lowers the real cost of the trip whether or not you ever use the insurance, as long as the booking goes ahead and is not cancelled.

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Frequently asked questions

Is there a way to get money back on travel insurance bought online?

Yes. Apart from a covered claim, there are two ways. Many US travel insurance plans have a free look period, often 10 to 15 days after purchase, when you can cancel for a full refund if you have not left on your trip or filed a claim. And before you buy the plan or book the trip, you can go through ShopBack US so part of what you pay comes back as cash.

What is the free look period on travel insurance?

It is a short window after you buy a plan when you can cancel it for a full refund of the plan cost. Generali Global Assistance, for example, says that for most states of residence this is 10 to 15 days from purchase, and 30 days for Indiana residents, as long as you have not filed a claim or left on your trip. Each insurer sets its own window within state rules, so read your plan document.

How much does cheap travel insurance cost in the US?

The US Travel Insurance Association says travel insurance generally costs 4 to 8 percent of the total trip cost, based on trip length, destination and the age of the traveler. On a 2,000 dollar trip that is roughly 80 to 160 dollars. Plans that cover less, such as post departure only plans, usually cost less.

Does Trip.com sell travel insurance in the US?

Yes. Trip.com's US site has a Travel Insurance section with plans from insurance partners. At the time of writing it featured a Vacation Package Travel Plan with trip cancellation up to 100 percent of trip cost and 50,000 dollars of emergency medical cover, and a Post Departure Travel Plan with trip interruption up to 100 percent of trip cost and 10,000 dollars of emergency medical cover, both with no deductible.

Is it cheaper to buy travel insurance on Booking.com or Expedia?

There is no fixed answer, because each protection quote is priced for your trip, your state and your travelers. The fair test is to take the quote shown at checkout and compare it with a standalone quote for the same trip cost, dates and travelers, then check what each plan covers before you pay.

Can I get cash back when I buy travel insurance online?

Often, yes, depending on where you buy. InsureMyTrip, a US site for comparing travel insurance plans, is a store on ShopBack US, so you can start from its ShopBack page, compare plans and buy in the same visit. For protection bought during a Booking.com, Expedia or Trip.com booking, what earns cash back is set out in the terms on that store's ShopBack page.

What happens to my cash back if I cancel the policy in the free look period?

A policy you cancel for a full refund usually no longer earns cash back, because cash back is paid on purchases you keep. If you are not sure you want the plan, decide inside the free look window and check the terms on the store's ShopBack page.

Do I need travel insurance if my booking has free cancellation?

You may need less of it. Trip cancellation cover repays prepaid costs you cannot get back, so a refundable hotel lowers the amount you need to insure. Medical, evacuation and baggage cover are separate, and the US Travel Insurance Association notes that many health plans may not cover you abroad or offer medical evacuation.

What is the cheapest way to book a trip and insure it?

Book refundable where the price gap is small, insure only the prepaid part you could lose, compare at least two insurance quotes for the same trip details, and open ShopBack as the last step before you book flights or hotels. Your effective price is what you pay minus the cash ShopBack returns.

Is cash back from ShopBack the same as airline miles or hotel points?

No. Cashback lowers what you actually pay for an order. It comes back as cash, so it works like a discount on the price, not like points or miles that you have to redeem with one company.

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Key takeaways

• Most US travel insurance has a free look period, often 10 to 15 days, for a full refund if you have not left or claimed.
• USTIA puts travel insurance at 4 to 8 percent of trip cost, so insuring only what you could lose is the main way to pay less.
• Trip.com sells its own travel plans on its US site; Expedia shows optional protection at checkout; many Booking.com stays offer free cancellation.
• InsureMyTrip is on ShopBack US for comparing plans; start from its ShopBack page before you buy.
• The last step before you book flights or hotels: open ShopBack. Your effective price is what you pay minus the cash ShopBack returns.

Booking the trip you plan to insure? Open the Expedia, Booking.com or Trip.com page on ShopBack US, check the live rate and terms, then book in the same visit.

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Related reads

• US Travel Cashback Hub
• Trip.com Discounts in the US
• How to Save on Expedia in the US
• Booking.com Discounts in the US
• Is Travel Insurance Really Worth the Cost?

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Disclaimer

The views and recommendations expressed in this article are those of the author. Travel insurance plans, free look periods, prices and covered reasons are set by each insurer and state and can change; read your plan document before you buy. Plan details quoted from Trip.com and Generali Global Assistance reflect their pages at the time of writing. Cash back rates and terms on ShopBack US are shown live on each store's ShopBack page.

This article is intended for general informational purposes only and should not be considered professional, insurance or financial advice.