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Flying internationally with Southwest Airlines

An overview of where Southwest flies to outside the U.S., and how you can save on your next trip


In recent years, Southwest Airlines has added a number of international destinations, including cities in Mexico, the Caribbean and Central America. If those destinations are on your list and you want to use miles and points to fly free, Southwest is a great option.

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Despite its name, Southwest Airlines flies to many more places than the American Southwest.

In recent years, the company has added a significant number of international destinations, but only within the Americas. Thus far, Southwest has largely targeted warm-weather destinations, including cities in Mexico, the Caribbean and Central America.

There’s been talk of flights to Canada and Europe, but with the recent addition of Hawaii to the list and the removal of the Boeing MAX 8 aircraft from service (which has reduced the number of Southwest planes available to fly), it doesn’t look like either of those places will be added anytime soon.

See related: How much are Southwest points worth?

Southwest international destinations

Here is the current list of international destinations you can reach on a Southwest Airlines flight:

  • Cabo San Lucas, Mexico
  • Cancun, Mexico
  • Cozumel, Mexico (starting in March 2020)
  • Puerto Vallarta, Mexico
  • Belize City, Belize
  • Liberia, Costa Rica
  • San Jose, Costa Rica
  • Havana, Cuba
  • Grand Cayman
  • Montego Bay, Jamaica
  • Aruba
  • Punta Cana, Dominican Republic
  • Turks and Caicos
  • Nassau, Bahamas

My family and I were recently at the all-inclusive Hilton La Romana Resort in the Dominican Republic, about 45 minutes from the resort town of Punta Cana, and we loved it. Many of Southwest’s international destinations truly feel like paradise with their crystal clear waters, beautiful beaches and abundant palm trees.

Is it practical to fly internationally with Southwest?

So far, we have only flown Southwest to Grand Cayman, though we currently have a flight booked for Turks and Caicos. We found it to be practical to fly Southwest to the Caribbean.

I recommend Southwest as the best airline for those who want to use miles and points to fly free for many reasons. The first of which is the Southwest Companion Pass, which lets one person fly free with you (aside from the mandatory government security fees of $5.60 per way in the U.S., though quite a bit more when flying internationally) for up to two years.

If you can earn a Southwest Companion Pass (it requires 125,000 qualifying points earned between Jan. 1 and Dec. 31 of any given year) you automatically eliminate the price of one person in your group to fly – either in points or dollars.

You can’t beat that savings flying any other airline. So even if a Southwest fare is more expensive than a competing airline, you’ll usually come out better with a companion pass because you’re essentially flying two for one. This is one of the key ways my family flies free most of the time.

I also like flying Southwest because the points price of a flight is based on the cash price, and Southwest fare prices fluctuate quite a bit. So if you pay attention, you can really get a bargain.

February tends to be the best time of year to score a deal on Southwest’s international flights, as it typically has a sale where prices hit rock bottom. Additionally, fall is a good season to snag a deal to these warm-weather destinations, as school is in session and they are less popular due to the risk of hurricanes.

Also, Southwest charges no fees to cancel or rebook a flight, so if the price drops after you purchase the fare, you can rebook. If you paid in dollars for its cheapest Wanna Get Away fare, you’ll get a Southwest credit back for the difference that must be used within one year and by the same person.

If you paid in points, the difference in the points price simply goes back into your account. We’ve saved tens of thousands of points over the years by simply continuing to check fare prices and rebooking if they’ve dropped.

See related: A complete guide to airline companion passes

How we fly Southwest to the Caribbean

We’ve flown Southwest to Grand Cayman, but we opted to fly to the island from Fort Lauderdale, Florida because the points price was so insanely cheap from there. From Fort Lauderdale to Grand Cayman, we paid only 2,160 points per person per way with my husband paying zero points because we added him using our companion pass.

Because flights were more than I wanted to pay on Southwest from our home airport to Fort Lauderdale, we opted to fly discount airline Allegiant to get to Florida. With fares, taxes and fees, it came to about $260 per person for us to get from Indianapolis to Grand Cayman. We will use the same method to get to Turks and Caicos, paying just 2,730 points per way from Fort Lauderdale.

Keep in mind that when flying internationally, you will pay a higher fee in one direction imposed by the country you’re flying to. This is usually about $80 one way and $5.60 the other way, so you’ll need to add that into the cost.

Should you use Southwest Rapid Rewards to book flights?

Yes, yes and yes! Again, by using the Southwest Companion Pass, you will save the cost of one person to fly every time. The easiest way to help earn the 125,000 points needed for the pass is to sign up for one personal Southwest credit card and one business Southwest credit card, such as the Southwest Rapid Rewards Premier Business Credit Card. Depending on their welcome bonus amounts at the time you sign up (and you hit the spend requirement in the required timeframe) you could be well on your way to earning the companion pass (or you could have enough to earn it outright with both bonuses combined).

If you earn the Southwest Companion Pass, you’ll also have those 125,000 points to book free flights as well. In the first year we held the pass, my family of four was able to fly to six U.S. destinations within one year using about 160,000 Southwest points, costing us less than $100 per flight for all four of us.

Those were not international destinations, which tend to be more expensive, but 125,000-plus points and a companion pass should easily get a family of four to at least one or two international destinations, plus taxes and fees.

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