This post contains references to products from one or more of our advertisers. We may receive compensation when you click on links to those products. For an explanation of our Advertising Policy, visit this page.
Update: Some offers mentioned below are no longer available. View the current offers here.
I used to fly Southwest a lot in college between Pittsburgh (where I went to school) and Philadelphia (home). It was pretty awesome – every 8 roundtrips gave me a free flight, which meant affordable visits to Las Vegas or wherever my alma mater (The University of Pittsburgh) was competing in a (admittedly lame) bowl game.
However, after I graduated and started traveling domestically for work, the allure of more domestic “free” travel wore off – I’d rather accrue traditional miles and use them for fancy international trips. While that’s still the case, Southwest is slowly starting to lure me back with flights now into LaGuardia and even between Fort Lauderdale and Islip, NY (great for the Hamptons and avoiding NYC traffic). From a family travel perspective, they still grant two free checked bags and free changes on paid tickets- something you won’t find anywhere else.
Well, the Southwest allure is heating up today, literally and figuratively, as they begin flying to numerous international destinations in the Caribbean, as I first reported back in January. Their first ever international flight took off from Baltimore to Aruba today, and another took off shortly thereafter from Baltimore to Montego Bay, Jamaica. Throughout the rest of the day there will be flights from Atlanta-Aruba; Atlanta-Montego Bay; Baltimore-Nassau, Bahamas; and Orlando-Montego Bay.
In November Southwest will also begin flying to Punta Cana, Cancun and Mexico City, per SWA.com:
- Atlanta and Punta Cana, from $165 one-way
- Austin and Cancun, from $168 one-way
- Baltimore/Washington and Punta Cana, from $195 one-way
- Chicago Midway and Cancun, from $178 one-way
- Chicago Midway and Montego Bay, from $159 one-way
- Chicago Midway and Punta Cana, from $195 one-way
- San Antonio and Mexico City, from $103 one-way
- Santa Ana/Orange County and Mexico City, from $133 one-way
This is great news for those with a boatload of Southwest points from their frequent 50,000 point credit cards offers, and especially those with the Southwest Companion Pass – one of the absolute most lucrative airline benefits out there today (for those who know how to maximize it).
For my needs, I’m still sticking with American Airlines Executive Platinum service because I value domestic and international upgrades and the strength of an international alliance, but if you’re looking for a solid airline with pretty good on-time stats, friendly crew and a simple loyalty program, now might be the time to take a longer look at Southwest.
Just a reminder: you can transfer Chase Ultimate Rewards points (from the Sapphire Preferred, Ink Plus and Ink Bold) instantly to Southwest at a 1:1 ratio (each point is worth ~1.5 cents apiece towards Wanna Get Away fares).
Hat tip to Today in the Sky who actually flew on the first Baltimore-Aruba flight!
For more on maximizing travel on Southwest and the Rapid Rewards program, check out these posts:
Know before you go.
News and deals straight to your inbox every day.