Three years ago, Low-Cost Carrier Southwest merged with its rival, AirTran. Combined, the airlines now carry more domestic passengers than any other. One of the key reasons Southwest bought AirTran in the first place was for AirTran’s attractive international routes – allowing Southwest International to come into existence, reaching coveted and higher-margin international markets.

Southwest International routes began going on sale Jan 27, 2014 (available for bookings), with flights starting in July between Atlanta and Aruba and Jamaica, Baltimore and Aruba and the Bahamas, and on Saturdays, between Orlando and Aruba and Montego Bay. By the end of July, Southwest International was possible out of Chicago’s Midway Airport and Montego Bay, Jamaica.

Southwest International’s first terminal broke ground at the William P. Hobby Airport in Houston (HOU) in September 2013. The first Southwest International flight out of this new terminal will be on March 7, 2015, between Houston and Aruba. The best part is that, since U.S. Border Patrol processes passengers in Aruba before they board to Houston, those passengers are able to land in Houston domestically – so essentially you will only see Houston International on the outbound journey, eliminating the need to go through customs back in the US.

A few weeks ago, Southwest International began offering flight options out of my home airport, Denver. I immediately went to http://www.southwest.com/international/ to check it out, thinking that there would be specific information on the Southwest International routes. On Southwest’s International page, there’s a banner called “Where and When”, which, when clicked, brings up a route map.

You’re prompted to choose your departure city, so I entered in Denver. Then the map of the cities and destinations and timeframe they’re available appear. OK, obvious I thought – that means Aruba, Cancun, Montego Bay, Nassau, and Cabo San Lucas will be available for me to book from Denver on Oct 7 (along with from the other US cities listed).

Not true. When I went to the Southwest flight booker to check out Southwest International routes, and tried DEN to Montego Bay, the booking failed.

When I tried DEN to Aruba, the booking failed.

Now I was getting frustrated. What flights did work from DEN, which was clearly advertised as being available starting Oct 7?

I decided to go about the searching another way – by checking out Southwest’s complete interactive route map: http://www.southwest.com/travel_center/routemap_dyn.html. This has got to be more helpful, I thought. I was able to click on DEN and set it to my origin – a good first step. Of course I assumed the tool would automatically filter out routes that weren’t bookable, but this wasn’t the case (Montego Bay still appeared). I was the left with the same conundrum of which routes I could actually book RIGHT NOW. Luckily, I chose right on my next guess with Cancun, and was able to price this combo out:

In the fine print, notice the following – verifying that the route map does show Southwest International routes that aren’t currently available:

• Southwest Airlines service to Mexico City and Punta Cana begins on November 2, 2014.
• Southwest Airlines service to San Jose, Costa Rica begins on March 7, 2015.

I would assume that most people would get frustrated (and give up earlier than I did) by Southwest’s inability to tell them what was actually available from their home city. Moreover, the error messages didn’t tell me anything useful either – Southwest could have provided the information I needed about the particular failed route in the error message, but unfortunately also lost out on this opportunity. In the end, I just went to Orbitz, which was much better at telling me what airlines were available for what routes concretely. And that means Southwest.com probably lost out on my booking.

Southwest International, can you please take the guess work out of your international route puzzle? Or at least provide the magic decoder ring such that I can actually book something in less than 5 minutes?

Besides vague and conflicting information around availability of routes,  some other challenges still exist from the Southwest-AirTran merger, and for Southwest International flight offerings:

• Dissimilar Ticketing system and back-end technology. This has made rebooking difficult for passengers wanting to take advantage of additional re-booking routes. Similarly, Southwest had to make changes to its booking and ticketing systems to offer International routes (which took several years since the merger to actually offer). In the beginning, Southwest International went to market keeping separate ticketing systems between AirTran and Southwest, but plans to have a unified system by end of this year (2014).
• Different prices and seat availability. For example, since the airlines now offer code-shares – you can actually book an AirTran flight through Southwest and by doing so take advantage of Southwest’s bags fly free (you would have had to pay for bags if you had booked through AirTran). So if you’re traveling to one of the international destinations now offered, make sure you find a way to do it through Southwest to avoid paying that baggage fee! The downside, of course, is that you won’t be able to reserve a seat.
• Early boarding not transferrable. Purchasing early boarding on Southwest doesn’t get you early boarding on connecting AirTran flights.
• Loyalty privileges. Frequent-flier points remain separate and Southwest companion passes (for high-tier flyers) can’t be used on AirTran.
• Baggage mishaps increasing. Since the merger, bags are increasingly not being delivered on the same flight as their owners – the mishandled rate was as high as 40% at one point last year. Hopefully, these kinks will get worked out as time foes on.
• Overbooking and complaints are up, too. Although, the rates are still lower than those for competitors.

My advice? Considering all the above, wait a little longer for the kinks to get worked out before trying out Southwest International. Unless of course the rates are just THAT GOOD that is can’t be passed up.