The ups and downs of flying Southwest-with 7 tips to make it easy

People either love or hate Southwest

The airline has a lot of fans, but there are many people who won’t go near it. I am have recently started flying Southwest again, and I will share some of my thoughts and tips with you. 

View from the plane when flying Southwest
On our way to LA, flying over the Bay Area

Flying Southwest-the Cons

I think there are a few different pain points with flying Southwest, in addition to the multiple flights issue. The “cattle call” nature of seat choosing can be a pain, since you don’t know where you are sitting or how soon you can get on the plane. Since the flights are short, there isn’t real food service, just snacks. The seats are super basic. Comfortable, but no charging jacks and no in-flight magazine! Finally, there are no first class or business seat options. 

Having to fly multiple flights is not fun. Although it is nice to be able to get off and stretch and grab something to eat, it makes the day longer and it can lead to difficulties if a plane is delayed. 

Flying Southwest-the pros

However, Southwest also has a very loyal fanbase and there are a lot of reasons why. First, the prices tend to be quite reasonable. If you watch for sales (which they will email you about), you can save yourself even more. Even if you have already booked a seat, you can cancel it, buy it again at a lower price, and get the difference refunded or issued to you in a flight credit that can be used for up to a year. There are no change fees even for the lowest rates. 

Unlike other low-cost airlines, Southwest doesn’t charge more for things like carry-on luggage or seat choices or refreshments. The seats are basic, but a pretty good size and pretty comfortable. 

Although Southwest doesn’t do meals, they do offer snacks and non-alcoholic drinks for free. They also have free movies and entertainment on some flights, which you can watch on your phone or computer. 

Of course, things have been rough during COVID, but overall their customer service is quite good. They consistently win awards for their quality. 

The Companion Pass is out of this world if you can get it: pretty much 2-for-1 for the current year and the next year, just pay tax and fees for the companion (usually about $20 or less). You can change your companion up to 3 times per year. And you can even use it if you are booking with points. People get the companion pass either by flying a lot or (more commonly) by signing up for a couple of Southwest credit cards. 

The best way to do this is to stagger it so you do the bulk of your minimum spend on each card at the tail end of one year and then finish the spend in January of the next year.

This gives you really close to 2 whole years of companion pass. It is tricky to do because a lot of people hit the limit on at least one card before the year’s up. It is imperative to understand the rules and keep really good records.

The worst is when someone hits the minimum on one card in December and doesn’t realize it and then doesn’t hit the second card until Jan. One bonus is in one year and the other in the next and they don’t have the points needed in a single year. No companion pass at all. 

I have never done the companion pass. If you are interested, here is a great article that walks you through it step-by-step from 10X Travel.

Southwest also doesn’t charge for checked bags, which is a departure from most of its domestic rivals. When flying Southwest, you can travel with a bag that fits in an overhead bin, a smaller bag that fits under the seat in front of you, and two checked bags, all for free!! This is an amazing amount of free luggage space!! 

Man standing with luggage at airpor
We could have brought so much more stuff if we wanted

The carryon must be smaller than 24” x 16” x 10”. This is larger than most other airlines, so if you already have a carryon bag you use elsewhere, it will likely fit. 

The personal item can be 16.25” x 13.5” x 8” in order to fit under the seat in front of you. You can get a decent backpack or messenger bag that will fit under the seat. 

I found these measurements on Southwest’s website. Please check to make sure they haven’t made changes before you pack!

Each checked bag can measure up to 62 inches total and weigh up to 50 pounds. If you have larger bags, it will cost $75 each bag each way. Again, check the website for updates.

I go back and forth on how I feel about the seating scheme. I think most people know how this works, but as a refresher: you enter the plane according to your boarding group. A, then B, then C. Not quite, because between A and B, they allow families traveling with children under 6 to board if they are in the B or C group, and active duty military, and maybe another designation or two. But in general, this is it.

Each group has 60 people. A1-30 boards first, then A31-60. There are markers at the gate to indicate numbering so that passengers can line up by number in order. 

The further you get from A1, the higher your chances of being crammed in the middle seat. 

On the one hand, it is stressful to not know where we will be sitting and where we will be in line. On the other, it seems like when I book seats with other airlines, I almost always end up sitting over the wing or way in the back because those are the only seats left when I book, or at the price point I am booking. I like having a window seat and seeing where we are going. So Southwest gives us a fighting chance. 

Why I like seeing where I am going


Flying Southwest-tips to make it easier

1. Carry on only

I know, I know. I just raved about their checked luggage policy. And it is great. But we try to have carryon only. First of all, it gets us out of the airport quicker. 

But second-Southwest relies on people doing short flights with lots of transfers. The number of transfers increases your chances that you will be delayed along the way, that a flight gets canceled, or that your delay causes you to miss a connection.

All of this puts your luggage in a little bit of jeopardy. For the most part, they are good at tracking luggage and pulling what needs to be pulled and rerouting to the correct plane. But still, I would rather not take chances. 

However, even though we do carryon, it is great to have the choice. If we go on our trip and find something big that we would like to buy and bring home, we always have the option to check something on the way home. 

This backpack easily fit under the seat

2. Use airport lounges

If you have a credit card that gives you lounge access, use the lounge in between flights. Lounges offer hot and cold food and even have some complimentary liquor options. They can provide a quiet(ish) place to sit and charge your devices. 

If you don’t have lounge access, scout Yelp or Tripadvisor before you fly to see what your best in-airport restaurants or snack shacks are. You can get a feel for the menus and pricing. 


3. Bring snacks

Whether or not you have club access or find a place to eat, bring snacks! Southwest’s snack options are very limited. We have a little soft cooler bag that we fill with prosciutto, string cheese, cubes of cheddar, and some rice crackers. Do not try to take fruit out of Hawaii though. Maybe get a very small jar of jam or yogurt cup instead.

When you are in between flights, try to find a quiet gate and sit and have your snack. It will help make everything better. 

The Centurion Lounge at the Oakland Airport. With the Dude’s food allergies, it is hard to find things to eat. So we pack our own, but we did get to enjoy some complimentary drinks.

4. Pack Gatorade packets

This tip has been so amazing. I get very dehydrated when flying or experiencing dry climates, and it can lead to headaches. I saw it suggested to pack Propel packets. I don’t like the taste of zero-calorie sweeteners, so I hunted high and low until I found a box of Gatorade powder packets. I went with individually wrapped single serving size pouches to avoid any potential hassle of getting a ziploc bag full of powder through TSA. I carry 5-6 of these in my backpack.

If I am feeling depleted, I mix it in my water bottle on the plane. I also have a bunch of them so if we are going to be somewhere hot, I can easily make myself a Gatorade when we are out and about. I haven’t ever used more than 1-3 on a trip, but it is nice to know they are there. 

5. Bring a power charger or charge at gate

Southwest has no outlets for passengers on their planes. A lot of times, layovers are in smaller airports that might not have great outlet options either. A power brick can be a life saver. You don’t have to hunt for a place to plug in and you can even charge on the plane while you are watching a movie. However, if you don’t have one, do remember to charge up as needed at connecting airports. 

6. Understand the 24-hour check in system or use the early bird

OK, this part is the most stressful part for me. I don’t even like watching competitive games, never mind participating in them!

As I mentioned earlier, if you can get into groups A or early B, you will have a much better shot at getting a seat you like and sitting next to your companion. 

So, how do you get the coveted A or early B (by early B, I mean B1-15, maybe a bit larger)? A1-15 is reserved for Business Select passengers. They get a few perks, but the coolest is that top of the line action. So those first spots are not usually available and we are already starting at A15. Don’t panic, remember these are large planes and there is still plenty of seating even if all of the Business Select folks spread out! 

If you have a lot of anxiety about getting a good position, or if you will not be available to check in at the 24-hour mark (more on that later), you can buy an Early-Bird Check In. This costs $15-$25 per person per way. If you do this, the system automatically checks you in 36 hours before flight time, so you have a good chance of being somewhere in the A-boarding group. 

It is best to buy this at the time you buy your tickets because it is a first-come, first-serve order, so if you buy the Early-Bird 2 months in advance, you will be closer to the front of the line than people who buy their Early Bird 2 weeks in advance. 

You can also be an A-lister if you have a Southwest credit card or fly a lot on the airline (currently 25 one way flights in a single year). A-list status gets you into the early bird check in time. 

They really try to be fun and engaging.


One important note-if you have a companion pass, you don’t have to buy an Early Bird for your companion because they will be checked in at the same time as you are.

Ok, so you are on Southwest, you didn’t buy a Business Select seat or Early Bird Check in and you are not in the A-List. What now?

Here is where your adrenaline-filled competitive skills come in handy. Southwest opens the check in process exactly 24 hours before your first flight. The longer it takes you to check in after the 24-hour mark, the further back your boarding pass is going to be. 

Make sure you have the Southwest app downloaded on your phone and on the phone of anyone flying with you. You can do it on the computer as well, but I think the app is a little faster and more direct. 

Set a calendar reminder with an audible alarm somewhere between 10 and 30 minutes before your check in time. Also (this is imperative): when you set that, also set one for the day before you are flying home. When you are on vacation, it is a lot harder to remember that check-in! 

About 10 minutes before check-in, open your app and click on your trip. Just keep it open. As you get to a few minutes before, refresh often to keep the phone awake. Watch the time. Once it hits the 24 hour mark, refresh the page and you will see a check in option. 

Click through it and bam! You are done! It gives you boarding passes for each leg of that flight. If you don’t see the “Check In” option, refresh again. Have each traveler do this at the same time and you will be able to board together. 

Save your passes to your Apple or Google Pay or just to your phone (the app has very easy save options right on the boarding pass page). 

As long as you are able to check in within the first few minutes of eligibility, you will likely be in the A or early B groups. 

7. Arrive on time

Now-this is very, very important-be at your gate on time!! Southwest starts boarding 30 minutes before departure. Remember that no seats are assigned. So even if you have an A1 spot, if you show up 15 minutes after boarding has started, you will be in the C group and will be sitting in the middle seat. Status only buys you the opportunity, it is not a guarantee. 

Hopefully you have an airport as nice as this to hang out at when you arrive early to make sure you get to your gate on time. PDX really is a lovely airport.


Once it is close to boarding time, the whole thing is quite orderly. The gate attendant will ask the A’s to line up by their designated markers, and that Bs and Cs stay seated until As are on. As passengers line up, folks will ask each other what number they have and everyone takes their place. 

Once the A31-60s start boarding, the first set of Bs start to line up, and it proceeds like this. The flight attendants help people find seats as the plane gets more full. 

So, with all the pros and cons, is flying Southwest worth it?

For us it definitely has been. When we went to Maui in the fall, our return flight was delayed and we spent a night in San Jose. Southwest covered our room in San Jose and gave us $600 in travel vouchers for our inconvenience. Between those vouchers, following Southwest sales carefully, and using my Amex Platinum flight vouchers (more on that in another post), we have really stretched our flight dollars. 

We have seen this view quite a bit lately


In the past year, we have spent about $1500 at When I just added it up, I said Ouch!! Because that is a lot of money! But then I did the breakdown. 

We currently have $350 in travel credits at Southwest, which we will use on future credit. So we have actually spent $1150 on flights. Still sounds like a lot. 

Where have we gone for $1150? So far, we have flown to Maui, Kauai, and Los Angeles. Each of these were 2 passengers roundtrip. In addition to the flights we have already taken, we will be going to Las Vegas in a couple of weeks.

This summer, the Dude will fly to Connecticut and then he and I will fly from Virginia back to PDX. I am flying to CT on a different airline, and we are trying out the Breeze between CT and VA. 

This works out to 4 roundtrips for 2 and a handful of one ways. Drilling down, it is 19 one way legs total. At $1150, that works out to about $60 per person per one-way trip. That includes all taxes and fees and baggage. For flying to Hawaii twice, across the country in the summer, and one flight the day after a holiday.

Even if we hadn’t received $600 in trip delay vouchers, it would still average out to about $90/one-way. 

With that said, I will look for other options when flying to Hawaii. Since there is no direct flight from PDX to Hawaii, having to fly to California adds hours to the travel days, and the potential for something going wrong and not having another option off or onto the island we are staying on is always there. However, I am not ruling out flying to Hawaii on Southwest again. And for continental flights, flying Southwest is a great way to get around on a budget.

As someone who wants to travel as much as I can, flying Southwest is a great tool in the toolbox!