These Air Canada Mistakes Cost Me $1,000
· 12 min. read
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This past December I flew from Regina to Winnipeg to Montreal. My return trip was from Montreal to Toronto to Regina. It was a standard flight, nothing too complicated. I only had carry-on luggage and one personal item (my backpack). My departing flight was with WestJet, while my return flight was with Air Canada.
My trip to Montreal went fine. The issue arose when I was returning home, departing Montreal.
My plane was supposed to leave at 6:15 pm, arriving in Toronto at 7:50 pm. I was then scheduled to depart Toronto at 9:05 pm and arrive in Regina at 11:28 pm. A long, almost six hours to get home.
However, about two hours before departing, my flight leaving Montreal was delayed 35 minutes due to "an earlier delay with the inbound scheduled aircraft", with a new departure time of 6:50 pm and a new arrival time of 7:33 pm. No problem, I still have lots of time to make my connection in Toronto.

While sitting on the plane in Montreal, in airplane mode, I would get three text messages and two emails from Air Canada. The emails are timestamped at 6:18 pm, meaning I got them while either waiting to board or waiting to depart. I would get the text messages at 7:39 pm, just minutes after landing and going off airplane mode.
The emails and texts said the following: the trip has been rebooked. I received a hotel voucher for the night, as well as two $15 meal vouchers. Most notable though, my new flight was rebooked to depart Toronto at 8:30 am, arriving in Vancouver at 10:30 am, and then departing Vancouver at 1:55 pm and arriving in Regina at 6:02 pm -- about 18 hours later than my original arrival time.


(Confusingly, I would get another email at 7:12 pm saying that my flight was not delayed, but I think this was just a mistake on their part because I had already been notified that it would be delayed.)
However, I should have taken this flight to Vancouver. This was the first mistake I made.
The reason is because of the Government of Canada's Air Passenger Protection Regulations and Air Canada's "Long Delay and Flight Cancellation Notice". If I do not fall under the following conditions:
- a) You do not have a confirmed reservation or are travelling on a fare that isn’t available, directly or indirectly, to the public;
- b) You are informed of the delay or cancellation at least 15 days before the scheduled time of departure;
- c) Your flight was delayed or cancelled due to situation outside of our control or required for safety purposes;
- d) You have already been paid denied boarding compensation;
- e) You have already been paid under another passenger rights regime for the same event;
- f) You failed to submit your claim within one year of the flight delay or cancellation.
Then, compensation for delays and cancellations is calculated based on your arrival time at the final destination and is:
- $400 CAD for delays at arrival between 3 and 6 hours;
- $700 CAD for delays at arrival between 6 and 9 hours; and
- $1,000 CAD for delays at arrival of 9 hours and more.
My delay was about 18 hours, so I would have fallen under the $1,000 compensation category. The caveat would be point C, if my flight was delayed due to cancellation outside of AirCanada's control. This is a bit of a grey area. My flight from Montreal to Toronto was delayed because of a delay with an inbound aircraft. My flight out of Toronto was delayed because of snow and freezing rain.
Once I got to Toronto and got my emails and text messages, I spoke to the gate attendant. AirCanada's algorithm determined a cross-continental voyage to Vancouver would have been the ideal trip, but there was another one that left around noon and got me straight to Regina by mid-afternoon. This was my second mistake. That wasn't really ideal, but looking back, it was the best option. This option got me to Regina the fastest, and still got me compensated $1,000.
Instead, I asked the gate attendant if I could switch airlines. I knew WestJet had a flight headed towards Regina that night, and I guess they weren't troubled by the snow and freezing rain like AirCanada was. The gate attendant told me I'd have to talk to a Ticketing Agent to do that. I got to the Ticketing Agents desk, but only other gate attendants were there. They pointed me up the stairs to some white, nondescript telephones where I could speak to somebody who could help me. I'm not sure who they were, so I can only assume it was a direct line to Oz. When I got through to somebody, the Voice of Oze either misspoke or my stressed system didn't hear it correctly, but I am certain they said that I could get a ticket with WestJet and then submit it as an expense to AirCanada. I mean, why not? It's either they pay for my flight with WestJet, or they reimburse me $1,000.
However, the Voice of Oz couldn't get me the ticket themselves. I'd have to get to the WestJet gate, buy a ticket, and then invoice AirCanada through their website via the reimbursement form. Sounds good. I then asked, since I won't be on the Toronto/Vancouver/Regina plane ride the following afternoon, should I request a refund? The Voice of Oz told me to make sure I got on the WestJet flight first because otherwise, I'd have no departing flight. This makes sense, so I said my goodbyes and headed across Toronto Pearson International Airport to the WestJet gate.

This is what I imagine they looked like.
A very sweaty 30 minutes later, I got to the WestJet counter and was able to book my flight. It was a last-minute flight and cost me $800. Ouch, but it would be reimbursed, so that's okay. Once I got to my gate, I took a photo of the receipt and submitted it to Air Canada, for an expense on the Toronto/Vancouver/Regina flight.
I would get on the WestJet plane, and fly home that night. I'd arrive in Regina, sleep, wake up, shower and have breakfast, and then contact AirCanads to put in my refund. I would only get about half my refund because I completed half my trip (Montreal to Toronto). That's fair, so I did that.
This was my third mistake.
Because I got a refund on my flight, I could not expense the costs incurred because of it.
I don't know why the Voice of Oz didn't pass on this logic to me, but it makes sense. So, I could not recover my $800 flight with WestJet. My employer (who paid for the original flights, as this was a work trip) would get a ~50% refund on the trip, which was about $150.
In their words:
"We reviewed your case and unfortunately you are not eligible to be reimbursed for the expenses you incurred during your trip with us. Our records confirm that you opted to fly your own way to your final destination, therefore, we have refunded the unused portion of your ticket back to the original form of payment on file."
But then, about five days later, I got the following email:
"We are in receipt of your claim for flight AC 423 YUL Montréal Trudeau - YYZ Toronto Pearson on 2024/12/14. We are sorry for the delay you experienced at arrival to your final destination.
You are entitled to a compensation amount of $400.00 CAD under the Air Passenger Protection Regulations in light of the delay you experienced. To accept your compensation in cash or in another form of compensation that has a greater monetary value than the cash amount, please access our online platform, developed in collaboration with our partner eConciliador, and select your preferred option.
Within the next 24 hours..."
I (who should really learn to stop questioning things) asked them to clarify because the Montreal to Toronto flight was only delayed for 35 minutes. It was my Toronto to Regina flight that was extremely delayed. I shouldn't be getting $400 for a 35-minute delay.
However, they clarified that I would be compensated $400 for my delayed flight from Montreal to Toronto, and a few days later, I received an Interac e-Transfer from them. I deposited the money, and my claim was closed.

I am not sure if it was an act of charity (I doubt it), but I don't know why I was compensated that amount of money. I think somebody made a mistake, may it be the Voice of Oz, since that conversation was recorded and could be used as evidence of our discussion, or maybe I misread Air Canada's "Long Delay and Flight Cancellation Notice".
Either way, had I either 1) taken the flight to Vancouver to Regina or 2) taken an alternative Air Canada flight to Regina or 3) not gotten a refund, I would have been eligible for a $1,000 flight compensation. Instead, I ended up being out about $400. It was a weird life lesson learned, but I thought I'd share it with you all. If you have any idea of what might have happened, I would love to hear your thoughts.
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Categories: Canada, General, Travel Tips
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