I fear that by the time you buy a Wine Check or other thing and/or pay porters and so forth to help you transport the case along, you’re going to spend more money and effort than the cost of one time overnighting one case of wine?
If handling the case of wine were doable for you, then checking it on the plane is the obvious solution.
Do you have some estimate of the actual overnight shipping cost? Maybe knowing that number helps us focus on whether an alternative is actually cheaper or not (or if the savings are enough to justify the strain of handling it on your travel).
Next day rates for a 19x18x14 box weighing 42 pounds:
$170 UPS discounted Pirate Ship rate
$484 FedEx undiscounted rate
If you really don’t want to spend the extra $100
…or buy a bag just for wine or have time to do so.
Southwest first bag is $35. Go to goodwill and buy a full size bag with good wheels for $7.
Ultimately I just leave it on the room with a note to take it or trash it for the cleaners
I’ve only done this with small bags (carry-on type) that fit a six pack styro. If you can’t fit two six styro (doubtful?) in the full bag I’m sure you ‘ll get one in there with the rest packed with bubble.
When you get off you have wheels and obviously more responsive help from everyone since it’s a bag of luggage and not just a heavy square box.
I posted about attempting this a bit ago and it works like a charm. I also don’t want to lug a typical cardboard case around the airport ect.
Two day AIR is usually cheap on pirate ship, If the temps are not 90+ ect I bet that would be a decent option.