Southwest Airlines: A Love Letter to the Airline That Keeps Travel Fun

The World Unfolding

Author

Jeff Rehmar
November 14, 2024

It's 8 a.m., and I’m in that special kind of travel daze where you’re not quite awake but definitely excited. I’m at Long Beach Airport (LGB), gearing up for a five-day adventure to Eugene, Oregon, with a quick layover in Sacramento. I’m not dreading the lines, the boarding process, or even the legroom because I know exactly what to expect with Southwest Airlines—a trip that’s going to be easy, reliable, and maybe even a little fun.

For those of us who live in California, Arizona, or Ohio, Southwest is the ultimate travel companion. They keep prices reasonable, schedules convenient, and boarding simple. It’s not just a flight; it’s a ticket to travel without the hassle. And if you’ve flown Southwest before, you know why they’re in a league of their own.

Open Seating: Like Finding a Great Table at Your Favorite Cafe

Flying Southwest feels like walking into your favorite neighborhood spot and picking out the best seat for yourself. There’s no upcharge for “priority” seats, no pressure to book the perfect spot months in advance. You get to board in groups, and then it’s open seating—pick any seat you like. Window seat? Sure thing. Want to sit near the wing? Go for it. It’s a small thrill in an era when every other airline seems determined to make you pay extra for a smidge more legroom.

But Southwest’s open-seating tradition won’t be around forever. They’re planning to shift to reserved seating by early 2026. I, for one, am going to savor every flight where I get to scope out my seat, feel the slight thrill of finding the perfect row, and settle in without any added fees. This unique boarding ritual has been a part of Southwest’s charm for so long, and it’s worth celebrating before it changes. Read more about Southwest’s switch to reserved seating on CNN.

All 737s, All the Time: No Surprises Here

Consistency is a gift in the chaotic world of travel, and Southwest gets it. Every plane in their fleet is a Boeing 737, meaning no surprise cramped regional jets, no mystery layouts, just the same solid 737 setup you’re used to. It’s like knowing the cafe you love always serves your favorite coffee blend. You know you’re getting a comfortable seat, enough legroom to actually enjoy the flight, and no unwelcome surprises when you board.

When you fly Southwest, you’re in familiar territory. Every time. It’s a detail that might not sound exciting at first, but anyone who’s ever been cramped into a regional jet knows it makes all the difference. And every once in a while, you might even luck out with an open middle seat—an unexpected bonus that can make an hour-long flight feel like first class.

Traveling with Friends, Football Fans, and the Friendliest Crew in the Skies

Recently, my flight up to Eugene, Oregon (EUG) was packed with football fans decked out in team colors, hyped for the game and creating an energy that felt more like a tailgate than a plane ride. This kind of atmosphere on other airlines might have felt overwhelming, maybe even annoying. But on Southwest, it felt downright enjoyable.

Why? Because Southwest crews lean into the vibe. The attendants added jokes to the safety announcement, threw in a few cheers for the fans, and treated us all like friends along for the same journey. These little touches turn a flight into something more than just travel—it’s an experience. When you board Southwest, you get more than a ticket; you get a relaxed, friendly vibe that makes the time fly (pun intended).

Two Free Checked Bags: Because Packing Shouldn’t Be a Negotiation

If you’ve ever flown with extra gear, you know how much of a struggle packing can be with most airlines. But Southwest? They make it easy. With two free checked bags, you don’t have to worry about fitting everything into one suitcase or paying a hefty fee for that extra bag. It’s just another way they make flying feel simple and fair.

So if you’re a golfer, a parent, or just someone who doesn’t like to pack light, Southwest has you covered. Two bags, no hidden fees, no stressing at check-in. Want to bring your clubs to Arizona? Planning to haul half your closet to Hawaii? With Southwest, it’s all included. In a world where “extra fees” seem to pop up everywhere, this policy is a breath of fresh air.

Red-Eye Flights Are Coming, But I’m Sticking to Daylight

If you’re like me and think sleep and air travel should work together, Southwest’s historic avoidance of red-eye flights has been a gift. For years, they’ve focused on flights at reasonable hours, making it easy to avoid those groggy, post-red-eye mornings.

But change is coming. Starting in February 2025, Southwest will introduce red-eye flights across 20 popular routes, giving night owls some new travel options. And while that’s a plus for those who want to maximize their time, I’ll be sticking to the day flights. Because if I’m going to travel, I want to enjoy it—not sleep through it. Catch more details about Southwest’s upcoming red-eye routes on The Points Guy.

Southwest Flies to Hawaii (and Makes It Easy to Pack for Paradise)

Since 2019, Southwest has added Hawaii to its destinations, opening up affordable access to paradise. For us West Coasters, this was a game-changer. Now, you can hop from San Diego, Oakland, San Jose, or Sacramento straight to Hawaii without breaking the bank. And they keep it real: the same no-frills, straightforward approach that works so well on their mainland flights translates beautifully for a tropical escape.

I’ve flown Southwest to Hawaii twice now, and both times, it was like getting a free pass to paradise. You still get two free checked bags (perfect for bringing extra beach gear), affordable fares, and the laid-back Southwest crew who make it feel like an easy trip. No fuss, just fun. And let’s face it: who doesn’t want a simple way to get to some of the world’s best beaches?

Price, Convenience, and Nonstop Options: The Big Three

If you’re choosing an airline, price, convenience, and nonstop options are likely your top three priorities. Southwest nails each of these. They keep fares competitive, and for those of us in Orange County, Phoenix, or even Cleveland, they’ve got plenty of routes, including nonstop options, to the places we’re actually trying to get to.

Living in Orange County, I get to choose between Long Beach (LGB) and John Wayne (SNA), and while both airports are great, LGB usually has the best prices. Southwest’s frequent flights and budget-friendly fares make it an easy choice, whether I’m headed up the coast or cross-country.

And for those of you in Phoenix, it’s a whole new level of convenience. Phoenix is one of Southwest’s focus cities, meaning tons of nonstop options and plenty of daily flights. You can book a trip to almost anywhere without dealing with too many connections, and the prices are rarely eye-watering. Cleveland, unfortunately, doesn’t have the same number of nonstop options—Southwest only flies to 9 nonstop cities from CLE—but they still offer solid fares for connecting routes to keep you covered.

Why Southwest Stands Out (And Why I Even Got the Credit Card)

Southwest Airlines isn’t just an airline; it’s a reminder that travel can still be simple, affordable, and fun. They’ve made air travel feel like a shared experience, from their friendly crews to their no-nonsense baggage policy. Even with some big changes on the horizon, like red-eye flights and reserved seating, they’ve kept what matters intact.

In fact, I liked Southwest’s approach so much that I got their credit card back in 2019. With every flight and every point earned, I feel like I’m building on a loyalty to an airline that genuinely values its passengers. For anyone who wants air travel to be efficient, affordable, and, just maybe, a little bit enjoyable, Southwest gets it right. Here’s to Southwest—the airline that makes travel easy and enjoyable, no matter where you’re headed.

Notes:

-I’ll be sharing poll results next week!

-I am not sponsored by Southwest Airlines.

As an update on my 10/31 newsletter: Why Congress Should Mandate Profit Sharing Between Men’s and Women’s Sports Leagues

For those following the conversation on gender equity in sports, here’s an interesting recent development: Women’s Baseball Players Form New League. This news highlights the increasing momentum behind women’s sports leagues and underscores why legislative support could play a crucial role in leveling the playing field.

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