Stopovers on Southwest?
 

Looking to go to Cancun from STL. Flight requires a connection and would not arrive until very late in the day. I know (at least I think) that Southwest doesn't allow stopovers. Could I just book a one way ticket to Atlanta, spend the night and have another one way ticket to Cancun early the next day?

Yes, they do not and yes you could.

Of course you can book 2 separate one ways...why couldn't you?

that is the only way you can do it on WN if a connection is not offered!

I have no idea why you couldn't. It seems logical that you would be able to but airlines aren't always logical.

A connection is offered I just don't want to arrive at my hotel at 7pm and waste the whole day.

I've done exactly that a few times already with Southwest when flying to the Caribbean from California. Just keep in mind that by booking two separate itineraries you are getting none of the advantages of having a connection. You'll have to re-clear security, you can't check bags through, and-- most importantly-- if anything happens with your first itinerary that makes you unable to be there on time for the second one, the risks and costs of dealing with that are all on you.

Not much risk of anything happening on the first itinerary. It's due to arrive in Atlanta at 5PM the day before and even if something did happen it's not the last scheduled flight that day.

As far as clearing security, wouldn't I have to go through customs before the flight to Cancun even if I booked it on one itinerary?

Aren't you kind of doing the same thing by spending the night mid-journey in Atlanta versus in Cancun? :confused:

That's what I was thinking as well. How much is 2 one-ways going to cost you, plus the hotel room, plus cabs if necessary, plus dinner and/or breakfast, in exchange for not "wasting" a day at the resort, where you'll still be there in time for dinner and drinks?

No. You clear immigration and customs (2 separate transactions) upon ENTERING a country (same upon returning to the USA).

You will need to make certain to get your passport verified and your outbound boarding pass stamped with the big red "documents OK" stamp at the Southwest gate podium.

Also be aware that if you have TSA Pre-Check, you will *not* receive it on your outbound Southwest International flight so plan accordingly re: getting thru security in the ATL. IT limitation within the airline.

Don't let silly worries get in the way. The fact that WN doesn't allow stopovers has nothing to do with re-clearing a TSA checkpoint at ATL. You need to reclear the checkpoint if you leave the airside area. You will do that if you have a stopover on a carrier which allows them, buy two OW's on WN, or go out for a smoke on a connection. So, nothing to worry about.

Whether the two OW's are the same as the through fare are the same is a different issue.

One positive to booking two separate one-ways is that, if you have TSA PreCheck, you will receive it on the domestic leg. You won't if you book a connecting flight.

It will not be on the same itinerary. Southwest doesn't allow overnight connections so I'm making my own. I'd rather get there at noon and be well rested because of a short 2 hour flight than arrive at 7PM and be tired from 8 hours of travel.

I'm using points and the difference between one flight with a connection and two one ways is negligible. The hotel is a Hyatt and is only 5000 points for the night. It offers free shuttle service to and from the hotel and offers free breakfast. So while there is some cost involved, it is minimal. And if spending an additional 5000 points allows me to spend 8 more hours at an all-inclusive resort, I think it is worth it. Not to mention I'll be well rested when I get there because I haven't spent all day traveling.