Air Canada made our itinerary impossible. Are we entitled to compensation?

I'll do my best to include the details without being too verbose.

1. Booked flight on Air Canada through skiplagged back in May. Original flight had 3 hours between arrival and departure from Toronto to Pittsburgh.
2. Never received any notice of changes to this itinerary from AC or Skiplagged
   1. according to the AC cx rep I spoke with this evening, the flight was cancelled back in June.
3. Went to check in this afternoon in Quebec and saw that our flight was an hour and a half later than initially scheduled. Further investigation revealed our flight from Toronto to Pittsburgh was half an hour from when we arrived in Toronto from Quebec. Impossible connection.
   1. originally our flight from Toronto was scheduled for 9:30, but the airline apparently cancelled this at some point and put us on a 6:30 departure from Toronto.
4. Talked w/ the Quebec Air Canada worker and she said they cancelled the originally scheduled flight and that there was no way we could make that flight. She said she would put a note on our file and that we can get vouchers from the airline once we miss the connection in Toronto.
5. Air Canada automatically rescheduled us on a flight for the next day leaving Toronto at noon and arriving in Pittsburgh around 10pm.
   1. This would make us about 25 hours late in our arrival to Pittsburgh.
6. After a couple hours on the phone, I got them to put us on a direct flight leaving tomorrow evening instead. At least now we aren't laid over in Chicago for 7 hours. We still arrive in Pittsburgh 21 hours later than initially planned.
7. Once we actually confirmed rescheduling our flight, we went and got vouchers for a hotel and about $40 in food.

I feel quite put out by the whole experience. We're going to end up having to spend additional money in Toronto (those airport food vouchers aren't going to cover an entire days worth of food for two people) and an additional day of parking once we get to Pittsburgh. We are forced to postpone a real estate closing that we've been working out for months. Not to mention losing a precious weekend day to traveling (this might be the worst part).

I ended up coming across some stuff about compensation for travelers in Canada who get delayed due to the circumstances within the airline's control. It seems like this would fall into that category, although I am unsure if somehow they can escape responsibility because Skiplagged was where the initial booking took place. The airline was certainly able to communicate other things to me (entry requirements, invitations to check in now, refunding GST, etc, automatic rescheduling this evening) so I'd expect they would be more than capable of conveying a cancellation/rescheduling in a timely fashion as well.

Is this something that may be eligible for compensation? Being delayed by almost 24 hours is throwing a big wrench into things.

Submitted September 25, 2021 at 12:59AM by distancingpattern https://ift.tt/3zAsK7r