This was during the arctic blast that occurred Christmas weekend.

Flying Air Canada from Raleigh to Winnipeg, had a number of cancellations and delays that wound me flying from Raleigh - Montreal - Toronto - Winnipeg, about 20 hours of travelling total. I had a brought a carry-on, seeing that the weather was not on my side, and I didn't want to lose it. Upon getting to the gate in Montreal, was immediately told to check in the bag, along with everyone else around me due to room. Not what I was hoping for but so be it. Except, the gate agent rushed me along to get in the plane (we had already been delayed more than four hours) and forgot to get me a confirmation receipt for the now checked luggage.

Upon getting to Winnipeg almost sixteen hours later, bag ended up not being there upon arrival. Who would have guessed. Unfortunately, the Air Canada service agents were of no help either and could only put a request in for me, and of course the phone lines were stuck on the, "At capacity" recording. Several weeks later, get a response from Air Canada basically giving me the run of, "From what we could see, it should've landed in Winnipeg, so we cannot investigate further or reimburse you. Sorry."

I put in a claim for Baggage Insurance through my Platinum, managed to get $800 back within three weeks. Simple process. Took a few times sending in documentation, but well worth it. Highly recommended if airlines are being a pain in the ass.