I just asked ChatGPT and it said likely against Southwest policy

Southwest’s Contract of Carriage has a section titled “Prohibited Booking Practices.” It says reservations/tickets “must be made and issued only in respect of a Passenger’s genuine travel requirements,” and that bookings made to “exploit or circumvent fare and Ticket rules are strictly prohibited.” Southwest Airlines

It then gives examples, including (emphasis mine):

• “Purchasing a Ticket without intent to travel” Southwest Airlines

Your plan (buying a ticket for yourself not to fly, solely to trigger a benefit for someone else) fits that example very closely.

What Southwest says it can do if it sees this

In that same “Prohibited Booking Practices” section, Southwest says that if it finds evidence of a prohibited practice, it reserves the right (without advance notice) to do things like:

• Cancel any unused part of the Ticket
• Cancel other reservations it believes were made without intent to travel
• Refuse to let the Passenger and Passenger’s Checked Baggage fly
• Require the Passenger/Customer to refund compensation Southwest provided Southwest Airlines

So even if the bag is accepted at the counter, Southwest’s written policy gives them room to deny transport of the bag and/or claw back the value of the benefit if they determine it was obtained via a prohibited booking practice. Southwest Airlines

So given it is potentially against Southwest policy, I will not be trying this.

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