Does Travel Insurance Actually Work? I Filed 6 Travel Insurance Claims From One Trip. 5 Paid Out (so far).
I’m going to be upfront with you. I did not plan to become a professional travel insurance claimant. I planned to spend twelve days in Costa Rica with family, add a four-night stopover in Montreal on the way back because the flights worked out cheapest that way, and return to Prague with nothing more than a sunburn and some good stories.
What I got instead was a masterclass in the gap between “travel insurance exists” and “does travel insurance actually work?” Six claims from a single trip. Four paid, two pending five paid, one pending. One of those pending is a formal complaint with the Canadian aviation authority, which is a sentence I never expected to write.
Let me walk you through the timeline because the timeline matters. The trip was: Prague to Costa Rica. Costa Rica to Montreal. Four nights in Montreal. Montreal back to Prague. The first domino fell three weeks before I even left.
(I document everything. Receipts, screenshots, confirmation numbers, the whole thing. I realize I sound like a conspiracy theorist. I’m just someone who has been burned before.)
The 6 Claims at a Glance: Financial Payout Breakdown
| # | Incident & Location | Provider / Benefit Used | Amount Claimed | Final Payout |
|---|---|---|---|---|
| 1 | Eye Infection (La Fortuna, Costa Rica) | Standalone Expat Policy | $160 USD | Paid in Full ($160 USD) |
| 2 | Flight Cancellation 3 wks prior (LIR → YUL) | Westjet / APPR Legal Complaint | ~$600 USD | Pending (CTA Backlog) |
| 3 | Overnight Weather Delay (YUL → YYZ) | Capital One Venture X Trip Delay | $500+ USD | Paid in Full ($500+ USD) |
| 4 | Involuntary Denied Boarding (Air Canada) | Air Canada APPR Mandatory Compensation | $900 CAD | Paid at Airport ($900 CAD) |
| 5 | Missed Tour (CN Tower Edgewalk) | Chase Sapphire Reserve Protection | $200+ CAD | Paid After Dispute ($200+ CAD) |
| 6 | Delayed Baggage (2 Days in Prague) | Air Canada Baggage Claim | $120 USD | Paid in Full (After 2 Mos) |
The Trip That Wouldn’t End
The itinerary, in full:
- Prague → Costa Rica. Twelve days with family. Hot springs, volcanoes, wildlife.
- Costa Rica (LIR) → Montreal (YUL). Four-night stopover.
- Montreal → Toronto → Prague. The return leg. This is where the wheels came off.
I left Prague with a checked bag, a carry-on, and a spreadsheet. I returned to Prague 22 days later with all of the above plus an eye infection, a $900 Air Canada payout, a $500 hotel reimbursement, and a pending complaint against Westjet that I am still actively pursuing.
Let me break it down claim by claim.
Claim #1: The Eye Infection — Costa Rica
Status: Paid — $160 USD
This happened on the first leg of the trip. Costa Rica. Thermal spa in La Fortuna. The water was warm. The minerals were rich. The bacteria were apparently also present.
I woke up the next morning with one eye swollen shut. I went to a local clinic. The doctor diagnosed it. Prescribed antibiotic drops. $120 for the consultation. $40 for the prescriptions. I got an official note and invoice from the doctor and pharmacy. I took photos of everything immediately. I let my insurance know I’d be sending a claim.
Got back to Prague. Sent the paperwork. Reimbursed. Easy.
The lesson: Medical claims are the most straightforward if you have documentation. Get the official note. Get the itemized invoice. Take photos before you leave the clinic. The insurance company is not going to argue with a doctor’s note.
More on the Costa Rica Itinerary
Claim #2: Westjet Flight Cancellation (Canadian APPR Regulations)
Status: Pending — Aviation Authority Complaint Filed
This is the one that made me angry.
Three weeks before flying from Liberia, Costa Rica (LIR) to Montreal (YUL), Westjet cancelled our flight. Under Canada’s Air Passenger Protection Regulations (APPR), airlines are legally required to rebook passengers on a competing airline if their own flight cannot get you to your destination within nine hours. Westjet refused and simply issued a cash refund, leaving me stranded with replacement tickets costing triple the original price.
The problem: prices were now three times what we originally paid. A refund doesn’t help when the replacement flight costs triple.
I called. I chatted. I quoted the actual law at them. I told them they were required to rebook me on another airline. They refused. Every single time.
I ended up buying the replacement flight for three times the original fare. I filed a complaint with the Canadian aviation authority. Apparently there’s a huge backlog. I’m still waiting.
The lesson: Airlines will violate APPR if they think you won’t fight it. Know your rights before you call. Quote the specific regulation. If they refuse, file the complaint. The backlog is real, but the process exists.
Claim #3: Weather Delay — How I Claimed $500 via Capital One Venture X Trip Delay Insurance
Status: Paid — $500+ via Capital One Venture X
On the return leg to Prague, we needed to go Montreal to Toronto, then Toronto to Prague. The Montreal-to-Toronto flight was cancelled while we were in the airport. Weather.
They gave us food vouchers. I immediately booked the Marriott adjacent to the airport. The price was going up fast because demand was skyrocketing. It went to over $500. Soon everything in the area was sold out. Booking immediately was the right call.
From there, I documented everything. Every meal. Every receipt. Itemized. Took photos immediately.
Filed through Capital One Venture X trip delay benefits. Overnight delay counts. The card covers up to $500 per covered passenger. I submitted the airline email showing the cancellation, the old boarding pass, the new boarding pass. Paid.
The lesson: When a weather cancellation happens, book your hotel immediately. Prices spike fast. Then document everything. The Venture X trip delay benefit is straightforward if you have the paperwork. Email from the airline showing cancellation. Old and new boarding passes. That’s it.
More on the Side Quest to Montreal
Claim #4: Air Canada Overbooked
Status: Paid — $900 CAD + Food Voucher
The next morning. Our newly scheduled flight to Toronto. Air Canada overbooked it. We got bumped.
Under APPR, that’s an immediate $900 CAD per passenger plus a food voucher. Air Canada was good about processing it in person. But there were a lot of passengers affected, so it was chaos. Each person took 30 to 45 minutes because they had to rebook everyone to their final destination and availability was changing constantly.
The gate agent was wonderful. She helped us. But it was tough.
The lesson: APPR denied boarding compensation is $900 CAD. It’s not a claim. It’s not a fight. They pay it at the airport. But if you’re one of many affected passengers, expect to wait. Be patient with the gate agent. They’re dealing with the same chaos you are.
Claim #5: Missed the CN Tower Edgewalk
Status: Paid — Over $200 CAD (After a Fight)
Because we missed our new flight (the overbooked one), we missed a tour we had booked in Toronto. The CN Tower Edgewalk. Over $200 CAD each. Not cheap.
I stupidly booked it on two different cards. But my Chase Sapphire Reserve has protection for missed tours caused by travel disruptions. The problem: they tried to classify it as an “event ticket” instead of a tour. Event tickets have different coverage. Tours don’t.
I had to fight back on that classification. I pointed out that Edgewalk is a ticketed experience, not a concert or a show. It’s a tour. They reclassified it. They paid.
The lesson: Credit card insurance companies will try to slot your claim into the category that pays less. If you know what your purchase actually was, push back. Be polite. Be specific. Cite the difference. They’ll reclassify it if you’re right.
Claim #6: Checked Bags Delayed Two Days
Status: Paid — Over Two Months
With the new flights Air Canada put us on, our checked bags didn’t make it to Prague until two days later. We needed toiletries. We went to the local pharmacies and drug stores. Bought about $120 worth of products.
Filed through Air Canada’s baggage claim process. Unlike the smooth processes from before, this one is was pending over two months later. They did deliver the luggage to the door. Finally, after two months, the cheque was in the mail, no pushback.
The lesson: Baggage claims are slow. The airline has no incentive to hurry. The only thing you can do is document everything. Receipts. Photos. The file number. Eventually they’ll process it. Eventually.
Does Travel Insurance Actually Work? How to File a Travel Insurance Claim (And Win).
I now have a six-step system. It looks excessive. It is probably excessive. But it works.
Here’s what I do on every trip now:
- Book flights on cards with good coverage. Venture X for flights. Chase Sapphire for tours and activities. Know the limits before you go.
- Book expenses on the same card. If your flight is on the Venture X, your hotel and meals go on the Venture X. Makes the claim traceable.
- Document everything. Immediately. Itemize. Take photos of receipts before you leave the counter. Email yourself the confirmation. Do it while you’re standing there.
- Know your rights, not just your coverage. APPR is not optional for airlines. If they violate it, file a complaint. The backlog is real but the process exists.
- Insurance companies will try to pay less. The Edgewalk claim got denied as an “event ticket.” I pushed back. They reclassified it. They paid. Be polite. Be specific. Know what you bought.
- Use AI to help. Use Gemini or ChatGPT to translate your policy into plain English. To draft your claim letters. To know your rights before you call the airline. It saves hours.
The math on the full trip: I spent about $1,800 in unexpected expenses between the replacement flight, the hotel, the toiletries, and the missed tour. I got back about $1,560 between paid claims. The two pending claims would add another $1,120 if they pay out.
I’m not saying travel insurance is a profit center. I’m saying the system works if you work the system. The first claim is the hardest. After that, you know the steps.
What Travel Insurance I Actually Use Now (And What I’d Recommend)
Here’s the honest part. My setup in Montreal was a patchwork. Venture X for the flight delay. Chase Sapphire for the Edgewalk claim. A separate travel insurance policy through our mortgage lender for the medical stuff. Each claim went to a different company. Each had different forms. Different limits. Different timelines.
It worked. But it was not elegant.
If I’m recommending something to someone who doesn’t want to maintain a spreadsheet of six credit card benefits and three insurance policies, or someone who isn’t covered by their card or bank, it’s SafetyWing.
The pitch, and it’s a short one: $62.72 every four weeks. Covers you in 180+ countries. Medical treatment, hospitalization, lost luggage up to $500 per item, travel delay coverage for unexpected overnight stays. You can buy it after you’ve already left your home country. No fixed dates. No itineraries. It’s a subscription. You’re covered until you cancel.
I still use my card benefits for the big stuff. Venture X trip delay is still better for hotel reimbursement.
If you’re a nomad, a freelancer, or just someone who travels enough that buying a new policy for every trip sounds exhausting, it’s worth the $62 every four weeks.
(Current price: ~$62.72 every four weeks for ages 18-39. I’d pay that honestly. It saves me the spreadsheet.)
Frequently Asked Questions About Travel Insurance Claims
Read about my $17 insurance saving me $42,000
Disclaimer: I am sharing my personal experience filing insurance and credit card claims. I am not a financial advisor or licensed insurance agent. Coverage terms vary by cardholder agreement and insurance provider. This post contains affiliate links (such as SafetyWing); if you purchase through them, I may earn a small commission at no additional cost to you.
