You're standing at the edge of the Southernmost Point buoy, a mojito in one hand and your phone in the other, trying to book a flight back home. You open your favorite airline app, the one with the blue and red heart, only to find... nothing. If you've ever typed "EYW" into the Southwest search bar, you've felt that specific sting of confusion.
Does Southwest Airlines fly to Key West? The short, blunt answer is no. As of early 2026, Southwest does not serve Key West International Airport.
It’s a bit of a bummer, honestly. We all love those two free checked bags—especially when you’re lugging back a suitcase full of sea shells and tacky "Conch Republic" t-shirts. But Southwest and the tiny, sun-drenched island of Key West have a complicated history. It’s like that ex who keeps showing up in your "People You May Know" feed even though you haven't talked in a decade.
The History: Why Southwest Left the Keys
It wasn't always this way. Back in 2012, Southwest acquired AirTran Airways. For a glorious, brief window, Southwest actually operated flights into Key West using the Boeing 737-700. It felt like a dream come true for budget travelers. You could fly from Orlando or Tampa directly into the heart of the island for less than a tank of gas.
But the honeymoon didn't last. By 2014, Southwest pulled the plug. Why? The logistics were a total nightmare.
Key West’s runway is notoriously short—only about 5,076 feet. For a massive 737, that’s like trying to land a semi-truck in a suburban driveway. To take off safely, Southwest often had to "weight restrict" their planes. Basically, they couldn't fill every seat or carry a full load of fuel. If you can't sell all the seats on a plane, you aren't making money. In the airline business, empty seats are the enemy.
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There were also reports that the humidity and salt air took a toll on the airframes, but mostly, it came down to the math. Southwest likes high-volume, "bus-stop" style routes. Key West is a boutique destination that requires precision and, quite frankly, smaller planes than Southwest wants to fly.
Where Southwest Flies in Florida Instead
If you’re a Southwest loyalist with a pile of Rapid Rewards points burning a hole in your pocket, don't give up on Florida just yet. You just have to be willing to drive a little.
Southwest has a massive footprint in the Sunshine State. You can still fly into these hubs and make your way south:
- Miami International Airport (MIA): This is your best bet. Southwest finally started flying here a few years back, and it's only about a 3.5-hour drive to Key West.
- Fort Lauderdale-Hollywood International (FLL): This is basically a Southwest stronghold. It’s slightly further north than Miami, but often cheaper.
- Fort Myers (RSW): A bit of a trek, but if you're planning to take the Key West Express ferry, this is the place to land.
- Tampa (TPA) and Orlando (MCO): These are great if you're doing a cross-Florida road trip, though the drive to the Keys from here is a solid 6 to 7 hours.
How to Actually Get to Key West in 2026
Since Southwest isn't an option, who is flying to the island? Surprisingly, the list is getting longer. Key West International Airport (EYW) has seen a massive expansion in the last two years.
American Airlines is the king of the island. They run non-stop flights from Miami, Charlotte, Dallas/Fort Worth, and even Philly. If you want the most options, you go with the silver bird.
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Delta and United also have a solid presence. Delta flies in from Atlanta and New York (LGA), while United brings people in from Houston, Chicago, and Newark.
But the real game-changers lately are the "budget-ish" carriers. JetBlue flies in from Boston and JFK. Allegiant Air has been adding routes like crazy from smaller cities like Cincinnati, Indianapolis, and even Pittsburgh. And then there's Breeze Airways, the new kid on the block, which recently started running flights from Orlando and Tampa—ironically filling the exact hole Southwest left behind.
The "Secret" Way: The Key West Express
If you absolutely insist on using your Southwest points to fly into Florida, look into the ferry. Fly Southwest into Fort Myers (RSW), take a 20-minute Uber to the docks, and hop on the Key West Express.
It’s a high-speed catamaran that takes about 3.5 hours. Honestly? It's better than flying. There’s a bar on board, you can sit on the deck and watch for dolphins, and you don't have to deal with TSA twice. By the time you dock at the foot of Elizabeth Street, you're already in a "vacation" headspace.
What Most People Get Wrong About Flying to Key West
A lot of travelers think that flying into Key West is always more expensive than driving from Miami. That’s a myth.
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Once you factor in the cost of a rental car (which are insanely pricey in Florida right now), the gas, and the $40-per-night parking fees at most Key West hotels, flying directly into EYW often ends up being cheaper. Plus, you save about 8 hours of round-trip driving time on the Overseas Highway.
The Overseas Highway is beautiful, sure. But it’s a two-lane road. One minor fender bender on a bridge can turn a 3-hour drive into a 7-hour crawl under the blazing sun. If you can find a deal on Delta or American, take the flight.
Actionable Next Steps
If you're planning a trip right now, here is exactly what you should do:
- Check the "Big Three": Look at American, Delta, and United first to see if they have direct flights from your home hub.
- Look at the "Hidden" Hubs: Check Silver Airways or Breeze if you’re already in Florida. They use smaller planes that handle the short Key West runway perfectly.
- Compare the "Drive vs. Fly": Calculate the rental car and parking costs before you commit to flying Southwest into Miami or Fort Lauderdale.
- Book the Ferry: If you do fly Southwest into Fort Myers, book your Key West Express tickets at least two weeks in advance, especially during the peak winter season.
Key West is worth the extra effort. Whether you arrive by a tiny puddle-jumper or a ferry with a margarita in hand, the island doesn't care how you got there—it just cares that you're ready to slow down.