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Hi,
I am flying Air Canada from YXE-FRA with a layover in YYZ on 24 Dec.
I am flying on a Christmas Eve flight so it might get quite empty on the plane. While checking-in, is it possible to ask the staff for a free upgrade from Economy Class to Executive Class?
I will use my Aegean Gold Card.

Free Upgrade while check-in
 

I highly doubt they would give you a FREE upgrade.

Yes, you may ask for anything, not just on Christmas Eve.

But, you're not gonna get it.

Free Upgrade while check-in
 

Good luck with that

You never know! When I was in South America recently I had 7 or 8 internal flights, all on Star Alliance airlines, all in economy. On the first flight I asked if an upgrade was available and noted I was Star Alliance Gold. My intention was to pay if it was not too expensive. Got it for free for myself and my wife. After that I proceeded to ask on every other flight (except for 2 where I was already upgraded at check in). Got it on all but 1 and remarkably, only had to pay for one, from Lima to Bogota. Coincidentally this was only 1 of 2 flights where I had to ask at the gate (the other one I asked for at the gate was also denied). For the others, I asked at check in. Quite frankly, I was amazed by this.

Motto: Never hurts to ask! ^

I think I went from Lima to Cusco (ug) to Puerto Maldonado (ug) to Cusco (ug) to Lima (ug) to Bogota (pd ug) to Quito (no) to Baltra (op up) to Quito (op up). Of course I attributed all my luck to experience gained on FT and the short holidays/mileage runs or bizarre routings I've taken over the years to maintain status. Mrs. Allbrosca said she would never bother me about it again :D

Free Upgrade while check-in
 

The gate agent has some discretionary power. If the plane is empty and no class upgrades are processed and she likes you for whatever reason she may be able to do so. Maybe business or a preferred seat who knows...
But showing some status card and asking for an upgrade cause you have such card wont charm her.

You wont get anything if you dont ask. Worst she can tell you is no.

YMMV. My boarding pass noted that I was Star Alliance Gold and I simply pointed it out. Perhaps I did so in a charming fashion. Whatever - it worked much to my surprise. :D

You won't get a free upgrade BUT you will very probably get a (relatively cheap) CASH upgrade - GO FOR IT! ^

The one upgrade I had to pay for could only be paid with CASH. I was told that there were no facilities for credit cards at the gate and that a receipt would be emailed to me but it must have wound up in my SPAM folder because I never saw it.

I find it more likely that your cash wound up in someone's pocket and the airline never saw it.

I think that's called a "tip" UG.

Yes, that also exists. But I guess it is illegal (for the airline employee).
But anyway: ACs real CASH upgrades are a bargain (if you pay cash or by credit card). I go for it whenever it is available ^

Hey! Thanks everyone for your comments.
I flew with them in January and so far they gave me free upgrade to Executive First Class on YYZ-FRA and MUC-YYZ! I did not even ask them. They just stopped me at the boarding gate and issued me a new boarding pass. Last week I also got upgraded from YEG to YVR. It all depends on how full the flight is in the economy class.

Wow. How many in J and Y? Ac almost never free ups it's own top tiers let alone cheapos from A3!

Gotta love A3:)