www.CostaRicaTicas.com

I always had to book point to point in order to get my trips put together. I found opening multiple browser windows to the southwest site and working backward was the way to go. I would go to the route tool which apparently is not working, then see where I wanted to go and where the flights went from that point. Now you know how they fly to your final destination. From there I would put in all the different airports and see what the costs were for the last leg of my trip. Once I found the one that worked for me, time-wise and lowest price I could now look at how to get to that destination in the US from an airport close to me. Just make sure your connections are within 4 hours so when you check in the counter people will combine your itinerary on 1 confirmation code and book your luggage all the way to your destination. If any one of your connections are more than 4 hours you will have to pick up your luggage at baggage claim and recheck them at that location.

Southwest is only operating one daily flight from Houston Hobby to SJO at this time. Departs at 4:40 pm. From Kansas City there is only one flight daily to Houston arriving at 9:55 am.

Other airlines will definitely give you the option to book a 6 hour layover. The Southwest website will say no flights available. Except Sunday when the first flight leaves KC 2 hours later, then I can book it directly.

As pointed out by Ilv4play sometimes you have to work the Southwest website checking all the point to points in your itinerary to truly understand your options and why they are telling you no flights when you know they are flying.

There has never been a DAL-SJO flight DAL doesn't have customs. There is flights every hour to HOU and then connect

That is correct. Only SWA non-stop to SJO from Texas is from HOU Hobby.

It was this way before COVID also.

here is a cool little tool I found it should work for all alirlines. It looks like Southworst is only connecting from Hobby to SJO or you need to go to Liberia from either Houston or Baltimore

https://www.flightconnections.com/route ... irlines-wn