Budget, Resources + Tools, Travel

4 Ways I Fly Stress-Free (+ how I save with Southwest while I do it)

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This one time, I stood in the TSA security line with Redfoo from LFMAO in the Columbus airport.

For reals.

Stuart still maintains it wasn’t him, but I knew better. It was totally Red Foo. Stuart thinks I was just excited for the honeymoon cruise, but I’d know that crazy afro anywhere. It was Redfoo, and I don’t know what he was doing in Columbus, but he was standing in front of us in the TSA security line and it took all I had not to break out in the Party Rock anthem.

He’s the only famous person I’ve ever seen in an airport. Then again, I’m usually trying to avoid making eye contact with anyone, so it’s possible I could have just missed any other chance encounters. Flying isn’t what it used to be, after all. Gone are the days of dressing to the nines for your luxurious Pan Am flight where leg room wasn’t an issue and being obnoxious would have all the ladies clutching their pearls.

You know, I wouldn’t mind wearing pantyhose, heels, and a suit–1940’s style–if it meant that flying wasn’t half the nightmare it is now. Instead, the rows get narrower, the people get grouchier, and the baggage fees get higher. And apparently everyone has decided a crowded airplane is the best place to act a fool. It seems like there have been more news stories involving airline drama, whether it be sitting on a tarmac for 4 hours, fights between passengers and the crew, or passengers being dragged off flights by security for various reasons. It’s enough to make me want to charter my own flights. But I’m not that wealthy…

So, what are we budget-conscious, wanderlust people supposed to do??

It takes some effort–and realization that not every airline is perfect–but do some research and find an airline that comes closest to aligning with your priorities.

Are you budget-conscious? Are you bare-bones and no-frills and you want the cheapest seat imaginable (which may or may not have the word, “Fed-Ex” or “cargo”, stamped somewhere on the plane)? Are baggage fees the bane of your existence? How much flexibility do you want? Will you absolutely lose it if you’re charged for a 1 oz bag of mini-pretzels (I mean, I would…)?

A couple years ago, after resigning myself to the notion that air travel just sucks, I finally took some advice and we booked our cruise flight to Tampa with Southwest. Some of you might have heard me say this before, but for those of you who haven’t, I’ll say it again (loud, for those in the back)…

If Southwest doesn’t fly there, I don’t want to go there.

4 Ways I Fly Stress-Free

It seems hyperbolic, but it’s actually worked for me thus far. And we love to travel! Some people make grandiose statements like this, but then they sneak off, do the opposite, and never tell anyone. But let me tell you something–brand loyalty is still a thing. I’m not talking about buying Dawn vs. Ajax, I’m talking about big-ticket items like airfare (like what I did there?). Lucky for us, Southwest flies A LOT of places in the continental U.S., including to the major international airports.

1. Plan Smart

I didn’t think much of vacation packages until I actually started looking into them. I thought, “Who cares? They just jack up the price and I’ll end up paying more than I would if I found my own hotel.” 

Not really. Depending on your destination, the time of year, and your hotel preferences, booking a flight and hotel package with Southwest Vacations could actually save you some major dough. They even have the option of adding car rentals and tickets to attractions (e.g., aquariums, etc.). For example, a 4-day winter vacay in January to one of my favorite cities, Tampa, plus lodging at the Holiday Inn & Suites in Clearwater Beach (p.s. we kind of love the Holiday Inn) came to a grand total of $720 with Southwest Vacations after an additional $100 promotional discount.

Now, if you’ve ever shopped for airfare, even without that promotional discount, you know that even $800 for flights and hotel for 2 people is a steal. I looked into how much this trip would cost if I booked the flights and hotel separately and this is what I found:

Roundtrip flights for 2 adults from Columbus to Tampa were $395 + $60 for Early Bird check-in (I’ll explain this soon) = $455. This was also impressive because I found Wanna Get Away flights for $92 one-way (winnnn!).

I found a standard room at the same Holiday Inn & Suites (the least expensive option) for the base rate of $148 per night x 3 nights = $444. This is not counting any hotel taxes and fees, so this total would actually be higher.

The trip I planned, booking flights and hotel separately, would cost at LEAST $899 (don’t forget those hotel taxes and fees) compared to the same vacation planned through Southwest Vacations, which would cost $720.

There’s also one thing to consider that many people will gladly pay extra for…

Convenience. If I can book each part of my trip in the same place, I’m more likely to do it even if it costs me a little extra. However, in this particular example, it would end up saving me money.

2. Opt for Early Bird Check-In (Do. It.)

This one time, I flew with another airline and didn’t realize that you had to sign back in before the flight and select the seats you want. As a result, I had to ask people if they would switch seats so I could sit next to my fiancee because I didn’t get the memo that this was a thing.

Seriously, why aren’t seats just assigned when you purchase your ticket? This seems completely inefficient, and super embarrassing if you’re not even aware of this concept…

Another reason why I like Southwest–there are no assigned seats. And if you opt for Early Bird check-in for $15 one-way ($30 per person on a roundtrip flight), Southwest will automatically check you in before the usual 24-hour check in time. This means that you will be in the first regular group to board the plane and you get to choose whichever seat you want and never have to worry about someone accidentally (or not accidentally) sitting in your seat by the time you get there.

Opt for Early Bird check-in every time, especially if you’re travelling with someone else. Don’t be those people who are last to get on the plane and hold everyone up because you’re looking for a group of seats that totally doesn’t exist because you were the ones who DIDN’T opt for Early Bird check-in.

3. Know Your Airfares

Southwest has three different kinds of airfares. I have to admit that, until recently, I didn’t know the difference except that I ALWAYS choose the least expensive one! Just remember–with roundtrips, you have to individually choose both the outgoing and returning flights. You pay the total at checkout, but you have to select each flight separately (which can be great because you can choose the time you prefer).

Business Select – More expensive, but you get extra Rapid Rewards and a premium drink on your day of travel. It’s the little things, amiright?? These tickets are also refundable and changeable, which means you can apply them to a future travel purchase with Southwest. So put on your pumps, order a Bloody Mary, and get professional.

Anytime – Less expensive than Business Select, and they’re also refundable, changeable, and can be applied to a future travel purchase with Southwest. This is a nice, safe, mid-priced fare because it still comes with options to change your travel plans if need be.

Wanna Get Away – I wanna flyyyy awayyyy, yeahhhh, yeahhhh, yeahhhh… Remember when Lenny Kravitz was the shiz? Anyway, this is the airfare I usually choose because it is SO cheap! However, you need to be sure your plans are set in stone because this fare is nonrefundable, but you can still apply it to a future travel purchase with Southwest. Seriously, my most recent ticket purchase for 2 adults from Columbus to Tucson (plus Early Bird check-in) was $600. No lies. That is CHEAP! So yeah, give me Wanna Get Away tickets all day long!

Except not, because I still have a mortgage to pay…

4. Simmer Down with the Packing

Once you plan your vacation, what do you pack? Seriously, this is kind of a big deal.

How about not your whole wardrobe because that can quickly become a nightmare. I used to over-pack, and then I tried to get uber minimal and that didn’t quite work out, either. Over the years, I’ve developed a standard packing list that I can adjust depending on the duration of my trip. I can’t stand packing a huge suitcase, but I need options!

The great thing about Southwest’s baggage fees are…

There are none. You’re welcome.

I got 99 problems, but baggage fees ain’t one…

But I’m pretty sure there’s still a weight limit, so you should probably consider that. Therefore, if you WANT to pack your entire wardrobe, you can (in 2 bags, for free!), but I still wouldn’t recommend it. Stuart and I like to pack light.

No, really, each time is like a new personal challenge. We each took 1 carry-on for a 7-day Caribbean cruise and seriously impressed the bell hops on the cruise ship (there was also a hair dryer and a pair of 4-inch wedge heels inside). And, by the way, if you take a cruise and have checked luggage, it will take hours for it to be delivered to your room. With a carry-on, you can take it right to your cabin, change into your beach-wear, and be sipping Mai Thais by the pool within 30 minutes of arrival.

For real, though.

I still can’t figure out why anyone would fly another airline besides Southwest. And when you consider their Southwest Vacations options, it’s obvious and you should have started packing yesterday. That being said, I have legit become obsessed with Southwest and their travel options ever since I took my first flight with them in 2016. I’m one of those creepy, obsessive planning people who plans random vacations in her head and then searches for hypothetical flights so I can gawk at the low prices and try to convince myself that we just HAVE to go on the trip because it’s such a good deal.

Anyone who knows me knows that I’m also the worst sales person on the planet. In high school I couldn’t even get a job at Macy’s because they worked on commission and I wasn’t convincing enough for that. If you don’t want to buy something, I’m the LAST person who’s going to try to con you into buying it unless I also think it’s awesome (cheapskate, party of one). However, when it comes to travelling and saving money, I’ll be the first person to give you the deets.

What can I say? I love to travel and save money while I do it.

Just remember–once your itinerary is settled, don’t over-pack and, if you think you see Redfoo in the airport…



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