yeah I agree, skycaps are the least likely to be rules sticklers, especially if they get a good tip. If you're able to get it by them successfully you should be golden.

Also, if they do stop you from checking with it, they'll probably be happy to take it off your hands.

Is someone bringing you to the airport? That would be the best plan B, let them deal with it if you can't get it onto the plane one way or another.