Southwest Airlines doing something it hasn’t done for four years | Official Website of Louis Velazquez, entrepreneur, finance guy and tech innovator

Southwest Airlines has done a lot of very unpopular things lately. The airline has ended its free checked bags, which were the hallmark of the brand and a big reason why Southwest had a loyal following. It’s also doing away with open seating, which was another big thing that set it apart from the crowd.

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Southwest is likely making these changes because it hasn’t been profitable since the fourth quarter of 2021. In the first quarter of 2025, for example, the airline experienced a net loss of $149 million.

While many of the changes that Southwest is making have drawn the anger of fans, not everything that the airline is doing is going to cause upset.

In fact, Southwest is doing something that the airline has not done in four years, since 2021,. And, this time, some flyers are likely going to be very excited about the upcoming action the airline is taking.

Southwest is making a big change and it’s a long-time coming.

Image source&colon; Tim Boyle/Getty Images

This is the first time that Southwest has made this move in four years

Southwest Airlines (LUV) is breaking a four-year-long streak of not adding any destinations to the list of places that the airline flies. Specifically, the company has announced that it will be adding service to Cyril E. King International Airport beginning in 2026.

This new airport is located in St. Thomas in the U.S. Virgin Islands. Southwest does need final regulatory approval to bring flights to St. Thomas. However, this is most likely not going to be an obstacle for the carrier at all. In fact, it is expected that Southwest is going to begin to sell tickets very soon to its new destination.

Adding its first new destination in four years is a major milestone that Southwest loyalists are likely to be excited about. Those who still prefer to fly Southwest Airlines will now be able to travel to a new vacation destination. And, as if that is not enough, adding the new flight to St. Thomas is just the beginning.

In fact, Southwest has made clear that this announcement was just the start, and it is expecting to add three new destinations in total for 2026. The carrier is going to be announcing the remaining locations sometime during the rest of the summer.

St. Thomas is likely to be a popular destination for Southwest flyers

Southwest’s addition of the St. Thomas Route is an unusual move just because of the fact that the airline has not added a new destination to its route plan in so long. However, it makes sense that St. Thomas would be the place that breaks this four-year-long lull.

St. Thomas is a logical addition to the airline’s lineup because Southwest already has nine island destinations that it serves. The airline already flies to Aruba, the Bahamas, the Cayman Islands, Cuba, the Dominican Republic, Jamaica, Puerto Rico, and Turks and Caicos.

In addition to these domestic flights, Southwest also offers international flights to Belize, as well as to three locations in Mexico and two in Costa Rica. The airline has indicated it is motivated to add St. Thomas to this list because it expects high customer demand.

“We are listening closely to what our Customers want—from new products and loyalty benefits to new destinations,” said Southwest Airlines CEO Bob Jordan. “We want to make Southwest Airlines the easy and obvious choice every time, and this is another meaningful step in our ongoing transformation.”

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So, if you are a Southwest flyer and you’re looking for a new vacation destination, take heart in knowing that Southwest has finally started adding routes after a long four-year hiatus, so now may be the perfect time to pack your bags and fly.