If you haven’t noticed, Southwest has been adding new markets left and right as of late. It’s been a long time since the airline did that, having previously moved up its entire multi-year plan to start during COVID. But now, with one exception, Southwest appears to be entering its leisure era, adding new dots to the map that Rapid Rewards members will want to visit.
Since 2012, Southwest has added an incredible 62 new airports to its route map, 50 of which are still here today. But those can generally be broken down into one of six eras. For all you Swifties out there, you’ll enjoy this.
The AirTran Era: 2012 – 2013
It was 2011 when Southwest bought AirTran to kill a lower-cost competitor. It did that quite well, but it also added a whole bunch of new domestic cities that were smaller than what Southwest was used to serving. It put its own B737s in these markets, and some of them worked. Others did not.
Maps generated by the Great Circle Mapper – copyright © Karl L. Swartz.
Ok, ok, so looking at this list today, the Washington/National (DCA) dot is not like the others. But it’s true that Southwest did not fly to DCA until it bought AirTran. It, of course, acquired more slots later. But for the rest of these, it was about adding service to more mid-size airports that didn’t fit the usual Southwest model.
With the exception of DCA, these are all pretty small markets for Southwest. Memphis is the biggest with about 12 daily flights. So while they were nice dots to add to the map, they weren’t all that significant in the scheme of things.
The International Era: 2014 – 2015 (ok, and a little 2017)
To be fair, this era of flying outside the US was really part two of the AirTran era. It took forever, but Southwest eventually coaxed its systems into being able to handle service outside the Continental US.
Southwest had a lot more success in this era, because these were markets that could easily fill a B737 with happy vacationers.
Maps generated by the Great Circle Mapper – copyright © Karl L. Swartz.
San Juan is about the same size as Memphis, and Cancún is even a little larger. But in general, these aren’t huge markets. Of course, the difference is that these are leisure markets where it’s almost entirely about destination traffic on peak leisure days.
What do I mean?
Full Year 2025 Southwest Departures by Day of Week
Data via Cirium
Not coincidentally, when Southwest started these international flights, it used its new Amadeus system, because it’s old system couldn’t handle it. The ability to better run day-of-week flying was key to making these markets work.
The only one that didn’t make it? That was Mexico City. Southwest may have improved its capabilities, but it never figured out how to take payment in Mexican Pesos (or any foreign currency). Let’s not even get into the schedule times. Unlike the rest, Mexico City was an origin market that just wasn’t going to work.
The Opportunistic Era: 2016
Yes, this is a bit of stretch to call this a single era, but it was in 2016 when two opportunities hit Southwest. It jumped into four new airports as a result.
The first was Cuba. When Cuba flying opened up, Southwest decided to dive right in. Not only did it serve Havana, but it also went into Santa Clara and Varadero. The latter two only made it into 2017. Havana itself is still flying today, but Southwest is only running a single daily flight from Tampa. That adventure hasn’t been a home run.
The second was Long Beach. When the airport’s noise dropped thanks to newer aircraft, more slots were opened up to fit within the noise ordinance. Southwest poked its nose in with Oakland flights and JetBlue… well, it didn’t go well for JetBlue. Over time, Southwest picked up more slots until today when it has nearly everything flying at the airport. With around 40 daily flights to 17 destinations, Long Beach is one of the bigger stations that Southwest has started in recent times. It does far better there than JetBlue ever did, but it’s also not a runaway success.
The Hawaiʻi Era: 2019
Just before the pandemic, Southwest finally got its fleet ETOPS certification and it began flying to Hawaiʻi. Not only did it go to the five biggest markets, but it flew between them too. This was a very big shift for Southwest.
For years, Southwest struggled to make this functional, but recently performance has improved. Q3 2024 was the first time the Hawaiʻi – mainland market produced stage length-adjusted unit revenue over 10 cents.
Maps generated by the Great Circle Mapper – copyright © Karl L. Swartz.
This may have some more maturing to do, but itʻs a key piece of the network for Southwest that isnʻt going anywhere. With more than 70 daily flights on average in 2025 that touched one of the islands on at least one end, this is a big investment. Southwestʻs rationale was that to really be able to win in California, you have to serve one of the most important leisure destinations from the state. This foreshadows what would come in the future.
The COVID Era: 2020 – 2021
Once COVID hit, airlines started losing money like crazy, but Southwest decided it would be crazy in a different way. It seems to have taken years of potential future growth markets and moved them forward into a 2020/2021 blizzard of madness.
Maps generated by the Great Circle Mapper – copyright © Karl L. Swartz.
These didnʻt all fall into one specific market type. You had the beach routes in the Southeast. There were the ski routes in the Mountain West. You had smaller cities on the West Coast. There were moves into primary airports where Southwest served the secondary: Chicago/OʻHare and Houston/IAH. Then there was Jackson. That must have been a political favor.
Some of these were wildly unsuccessful. Those four red dots on the map were cut very quickly once the airline started getting pressure from its investors (ahem, Elliott) to clean up its act. There was no time to wait for them to mature.
Others have struggled. Thereʻs OʻHare which has already seen multiple different strategies tried with different routes. Or thereʻs Palm Springs which already lost Portland (OR) and Phoenix but gained Austin and Chicago/Midway. This has been one big trial-and-error session. Itʻs not easy trying to mature so many markets at once.
The biggest of these markets that remain? Miami and Sarasota along with Colorado Springs and OʻHare.
The Leisure Era: 2025 –
Southwestʻs last new city started in 2021, and then there was a five-year break. But starting this year, Southwest began adding new cities to the map. And so far, it looks like weʻre entering the leisure era for the airline. We have, of course, already seen this before with The International Era and some of the COVID markets, but this seems to be a bit more of a focused effort.
St Thomas and St Maarten in the Caribbean begin next year, as do Anchorage and Santa Rosa in the West. Santa Rosa may have some more local appeal than the others will, but this still pretty clearly looks like a destination strategy. The only outlier? Knoxville. Sure, some of you may be going to see the Wigsphere Sunsphere, but thatʻs probably more similar to the markets of The AirTran Era than anything else.
The difference now? That sweet, sweet loyalty money is too big to ignore. Southwest wants those dots on the map so you can use Rapid Rewards points to drink wine in Napa with your friends, go on an Alaskan cruise, watch airplanes on Maho Beach (no? is that just me?), or do whatever people do in St Thomas.
I imagine there will be more coming to the network before this era comes to a close.
