Greetings!
See my post dated November 30 on this thread.
The general cause of email delivery failures is either an incorrect email address was entered or some kind of spam filter on the user's account or network is erroneously blocking the confirmation email from coming through. Unfortunately, this is usually the buyer's responsibility, not the seller which I suspect why Chase denied the dispute. If you’ve been charged and the transaction posts to your statement, the seller should have record of the transaction.
SW Hotels bookings are powered through Booking.com, not directly through Southwest Airlines. Unfortunately, Southwest Airlines Customer Service cannot assist directly with SW Hotels bookings although I do agree that SW Customer Service should have a means to transfer callers to a Booking.com rep for SW Hotel inquiries. Same can be said for SW Vacations bookings to a Apple Leisure Group rep.
SW Hotels has a dedicated concierge line posted on their website and in the confirmation email (also posted in my original reply). Did you try contacting this number prior to starting a dispute with Chase? Let the Booking.com rep know that you booked a hotel room for the specific dates you requested through Southwest Hotels but never received the confirmation email or number but were billed for the transaction. Give the rep the exact amount. If the rep cannot help you, ask that you speak to somebody in a supervisory position who may be able to look this up for you. Provide them with your name and email address too as confirmation. The fact that you were billed indicates they should have record of the transaction in question.
As stated in my reply...and this general advice would apply to any kind of online reservation whether it be air travel, hotel, or even pre-paying for parking...Always save (via screenshot or print to PDF) or do a hard copy print of the confirmation screen following the purchase in case the confirmation email fails to deliver. For Southwest Hotels, that would be the "You're All Set" page in conjunction with the linked PDF receipt. Save 'em before closing the window.
And a personal tip...I always pay the extra few dollars and opt for Free Cancellation. I don't normally buy travel insurance but having the Free Cancellation "insurance" is well worth it in case of a booking error, change of plans, or if prices later drop.
