For the longest time, the answer was a flat no. You'd pull up the Southwest route map, squint at the Caribbean, and see a big empty space where St. Thomas and St. Croix should be. It was frustrating for those of us who hoard Rapid Rewards points like dragons guarding gold.
But things just changed.
Does Southwest Airlines fly to the US Virgin Islands? Yes, as of February 2026, Southwest has officially entered the market. It’s a huge deal for anyone who prefers the "bags fly free" lifestyle over paying fifty bucks just to pack a pair of flip-flops.
The New Reality of Southwest in the USVI
Southwest finally pulled the trigger on service to St. Thomas (STT). They’re flying into Cyril E. King International Airport, which is basically the gateway to the rest of the islands. If you’ve been waiting to use your Companion Pass to hit M weekends in the islands, the window is finally open.
They aren't just dipping their toes in, either. They’ve launched daily nonstop service from two major hubs:
- Orlando (MCO): This is the big one. Since Orlando is a massive Southwest fortress, it makes connecting from almost anywhere in the Midwest or South pretty easy.
- Baltimore/Washington (BWI): Ideal for the East Coast crowd. If you're coming from the Northeast, this is likely where you'll be switching planes.
Honestly, it’s about time. For years, we had to rely on Spirit, JetBlue, or the "Big Three" (American, Delta, United) to get down there. Having Southwest in the mix usually forces prices down across the board. Competition is a beautiful thing for our wallets.
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What about St. Croix?
Here is the catch. While Southwest is now firmly planted in St. Thomas, they haven't started flying into St. Croix (STX) yet.
If your heart is set on the "Big Island," you'll have to fly Southwest into St. Thomas and then hop on a "puddle jumper." Cape Air and Silver Airways do these runs constantly. It’s a 20-minute flight, and the views of the reef from those small planes are actually better than the vacation itself sometimes. Or, you can take the QE IV ferry, but check the weather first—the Caribbean Sea can get spicy.
Why This Change Matters for Your Points
Before 2026, your Rapid Rewards points were basically useless for the USVI. You could fly to San Juan, Puerto Rico (SJU), and then pay cash for a separate ticket to St. Thomas, but that’s a hassle. You’d have to exit security, grab your bags, re-check them, and pray your first flight wasn't delayed.
Now, you can book the whole thing on one itinerary. If Southwest delays your flight into Orlando, it’s on them to get you to St. Thomas. That peace of mind is worth a lot when you're headed to paradise.
Also, don't forget the no passport required factor. Since the US Virgin Islands are a US Territory, you don't need a passport if you're a US citizen. You just show up with your driver's license. It’s like flying to Florida, but with better rum and steeper hills.
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Navigating the Southwest Experience in 2026
Southwest isn't exactly the same airline it was a few years ago. If you haven't flown them recently, you might be in for a surprise. They’ve moved toward assigned seating—yeah, the "hunger games" of boarding is mostly a thing of the past now.
When you book your flight to St. Thomas, you’ll see a few changes:
- Assigned Seats: No more lining up at the pillars like you're waiting for a bus.
- Premium Options: They now have seats with extra legroom. For a four-hour flight from Baltimore, your knees will thank you.
- The Bags Still Fly Free: This is the GOAT of airline policies. You get two checked bags. When you're packing snorkel gear, reef-safe sunscreen, and enough clothes for a week, that’s a savings of $120+ round trip.
Booking Tips for St. Thomas
Southwest tends to release their schedule in big "batches." If you try to book a flight for Christmas 2026 right now, you might see nothing. You have to keep an eye on their "Releases" page. Usually, they sell out the cheapest "Wanna Get Away" fares to the Caribbean within days of the schedule opening.
Comparison: Southwest vs. The Competition
So, is it actually better to fly Southwest to the USVI?
American Airlines still owns the most "real estate" in the islands. They fly from Miami, Charlotte, Dallas, and New York. If you live in a hub city for AA, it might still be faster. But you’ll pay for those bags.
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Spirit and Frontier also fly there, often for "dirt cheap" base fares. But once you add a carry-on, a checked bag, and a seat selection, that $80 flight magically turns into $250.
Southwest’s value is in the transparency. What you see is what you pay. Plus, if you need to cancel at the last minute because of a hurricane or a change of heart, you get your money back as a flight credit that never expires. Most other airlines will charge you a "re-fleeting fee" or some other nonsense.
Actionable Steps for Your Tropical Trip
If you’re ready to pull the trigger on a USVI trip using Southwest, here’s how to do it right:
- Check BWI and MCO first: Even if you don't live there, check the fares from these hubs. Sometimes it’s cheaper to buy a "positioning flight" to Orlando and then a separate ticket to St. Thomas.
- Download the App: Southwest's website can be a bit clunky on mobile. The app is way faster for checking those "Wanna Get Away" deals.
- Watch the Tuesday/Wednesday Window: Historically, Southwest drops their lowest fares for mid-week travel. Flying on a Saturday to St. Thomas is always going to be the most expensive way to do it.
- Factor in the Ferry: If you're staying on St. John, remember that Southwest gets you to St. Thomas. You still need to take a taxi to Red Hook and catch the ferry to Cruz Bay. Build in at least two hours for that transition.
The arrival of Southwest in the US Virgin Islands is a game-changer for budget-conscious travelers. It makes the islands more accessible, keeps the other airlines honest with their pricing, and finally gives us a way to use those points for something other than a flight to Phoenix. Start checking those dates; the beaches are waiting.
Next Steps
To get the most out of your trip, check the Southwest "Low Fare Calendar" specifically for the Orlando to St. Thomas route. If you're looking to visit St. Croix, you should also research the current schedule for Cape Air to ensure your connection in St. Thomas doesn't involve a four-hour wait at the airport bar—though there are worse places to be stuck.