Points, Miles & Life

Travel adventures on this earthly pilgrimage

Category: Southwest

Our First Time Flying with Kids

On Saturday my wife and I *finally* returned to the U.S. with our kids. The adoption trip was long, and we almost didn’t get to come home on the Southwest flights we booked. But in the end it all worked out exactly as we hoped.

The trip was our first time flying with kids. We’ve traveled plenty as a couple, and at this point the process is routine. But traveling with three children is an entirely different experience. We were a bit worried how our kids would react to their first time on a plane. Overall, our trip went quite well, something for which I am extremely grateful.

Much of our success is likely due to the fact that our children (thankfully) didn’t have any severe anxiety about flying and are well behaved on the whole. But part of our success can likely be attributed to some proactive measure we took. Here is the rundown on our first time flying with kids.

Combating kids’ fears of flying

Our kids were a bit nervous about their first flight, but they were also excited. I tried to play off the latter as much as possible. Over a few weeks before the trip, I took some time to show them some photos of us on previous flights, some YouTube videos of takeoff, and pictures of airports.

Even with those measures, they still expressed some doubts and fears. The question at the forefront of their minds was the safety of the experience. They seemed a bit incredulous when I explained to them that flying is safer than driving in a car. That age-old issue of perceived versus actual risk.

Since statistics are impossible for them to fully comprehend, I switched to relying on personal experience. I told them that I have flown a good amount (LOL – a mere 120,000 miles) and have never been on a flight that has had serious problems. My one diverted flight doesn’t really count since it was due to a medical emergency.

Checking all the baggage and navigating security

We arrived at SJO airport with our six checked bags, one carry on, and five personal items. This was waaaay more luggage than I’ve ever wanted. We brought FOUR checked bags to Costa Rica. Sadly, we had to buy one more to fit all our kids’ stuff. Adding in my mother-in-law’s bag finished the half dozen. I hope to never, ever travel with this much luggage again.

Fortunately, we were flying Southwest, so the ridiculous amount of luggage didn’t cost us anything. The kids were eager to roll around a bag, so that took one off our hands. The toddler worked against us, though, as he insisted on carrying the backpack we’d (over)packed for him, but needed mom to help hold it up with one hand.

The kids curiosity morphed into restlessness at the check-in counter since things took so long. One bag was 55 pounds, so we had to do the last-minute shuffle with the contents (I’m sure everyone else in line hated us). Since the three kids were pretty much only getting in the way, I finally had them go wait with grandma. This is when I reminded myself that I needed to talk them through everything.

Taking time to explain things

Kids definitely do best when you explain the plan to them ahead of time. It was amazing how much better things went once we got all of us into a routine during our stay in Costa Rica. Knowing what is coming next helps them immensely.

When we are about to do something new (such as flying), I try to explain the situation and experience as much as possible. I also try to brief them on potential problems we may encounter. This is a great thing to do for activities beyond flying, but it definitely helped us during our first time flying with kids.

As we navigated the airport and plane, I did my best to explain each part of the process to them. First, it was the security experience. Then waiting at the gate (or going on little walks in the terminal) before boarding. Finally, boarding the aircraft. Talking them through things really helped everything go smoothly and made our first time flying with kids much easier.


Boarding our first flight!

One of the benefits of flying Southwest is the family boarding process. Even though we were assigned boarding positions in the high Bs, we still took advantage of the Family Boarding offered between the A and B groups. Our kids were 3, 7 (barely), and 10, and going by the book, they should have only let one of us board with the youngest. However, the gate agent was very gracious, and we all boarded together.

The kids were super excited as we walked the jetway.

first time flying with kids

I was ecstatic that this was the dominant reaction instead of fear.

Since there were plenty of empty seats when we boarded, we were able to settle into a single row across the plane. Arranging seats as a group of six on a 737 is easy. I sat with the older two while mom and grandma managed the toddler.

first time flying with kids

The kids oohed and aahed a bit at the other planes, especially any they saw moving. San José airport isn’t all that busy (compared to say, SFO), so we only really got to see one other plane take off.

Taxi and takeoff

The kids’ excitement went up a few more notches the instant we started moving. They were both glued to the window. I was just as excited, but more so because taking off meant we were actually headed home.

Our three-year-old was hands-down the most excited. He didn’t take his eyes off the window. Every single plane he saw as we taxied was just as exciting as the previous one. He probably shouted “avión!” a dozen times.

No, he was not seated like this for takeoff

The looks on the kids’ faces was priceless when the plane started accelerating down the runway. Like with everything else, I tried to give the kids a little heads up that we were about to take off and what it would feel like. When the engines spooled up and we started hurtling down the runway, they were all smiles.

Once we were airborne, there was even more excitement as they pointed at the buildings below and at the hills of their beautiful country. With all the change that had happened to them in so short a time, I was thankful to see them smiling and laughing.

Soon we’d climbed into the clouds. With nothing left to view, the kids started digging through their bags for stuff with which to play.

What can you pack besides electronics?

This may be a hard road, but we’re trying to heavily limit our kids’ electronics intake in general. We had an iPad on hand with a couple movies loaded on it, but we hoped the kids could entertain themselves with other things for most of the flight.

My wife packed all three kids’ backpacks with various toys, drawing pads, and snacks. We made sure to hide them so that they would be a surprise for the trip. As we were leaving the hotel, we gave them the backpacks. Even then we made them wait to open them until we were seated at the gate.

The whole idea worked quite well. They *loved* discovering what we had packed for them, and their new toys kept them entertained for quite a while on our flight to Houston. I did break out the iPad for music.

A definite winner was the Boogie Board drawing pad (which I guess is technically electronic). The kids could draw as much as they liked, but without the hassle of pens or pencils and paper. It even allowed us to play several rounds of tic-tac-toe and other games.

In the air – our first time flying with kids

My biggest concern was our *very* active three-year-old who has trouble sitting still for anything. Two 4-hours flights might have been a very long day.

Things started out well.  The little man had two adults to help entertain him, and he had snacks to eat. I got my hopes up that it might be smooth sailing the whole trip.

Alas, this was too much to ask. About an hour into the flight we had our first round of tears. He was getting squirmy, and mom finally had to hold him for a bit. How upsetting that is. Luckily, he doesn’t usually throw a fit for more than minute or two, and soon he was back to playing with his stuffed dinosaur.

There were a couple more incidents of excessive squirming and a few more bouts of tears due to making him sit so long. Fortunately, his crying is subdued enough that I wasn’t worried about it bothering other people too much. It wasn’t an intentional choice, but we’d also managed to sandwich ourselves between two other families, one of which had a lap child. I’m sure they understood completely, if they even noticed.

When a patch of turbulence hit, I got a bit worried. I thought our kids might freak out. But they really didn’t react at all. Granted, it wasn’t all that strong, but I was thankful that this wasn’t an issue (NOTE: on our second flight, a patch of turbulence did end up making our ten-year-old scream). The more frequent comment we got was that it didn’t feel like we were moving at all.

The fact that Southwest also loaded us up with snacks every chance they could (I don’t remember this from previous experiences?) really made the kids’ day. Sure, we didn’t think that a diet of chips and coke is the best thing for them, but hey, we wanted them to enjoy the experience.

My daughter did remark that she enjoyed flying much more than driving (yay!). Why? Apparently, it was because I wasn’t telling them “I can’t talk right now” at all. San José traffic and Costa Rica’s mountain roads often required all my concentration, and this is my standard response when they barrage me with questions.

Teaching our kids basic flying etiquette

I couldn’t help myself on this one. As things seemed to be going smoothly enough (i.e. our first time flying with kids was in fun mode and not survival mode), I figured it would be good to start teaching the kids good flying etiquette.

We ran through the basic stuff first: getting out of the aisle, stowing under-seat luggage, not reclining the seat before takeoff. I also ran through seat items such as seatbelt use, air vents (I had to help them, obviously), and the reading light and flight attendant call buttons. I instructed them not to tough the latter.  The older two listened well and did just fine.

Later on, I tackled some other items, such as being gentle when opening and closing the tray table and not using the seats in front of you as a hand hold getting up or down. The latter is a major pet peeve of mine. It turned out that the kids never asked to recline the seat (nor did the people in front of us), so we didn’t have to deal with that at all.

They did well, and I’m sure they will get even better on subsequent fights. But on Day 1, I already feel like they are air travel all-stars.

Landing in Houston

The kids became excited as we started to descend. This quickly turned to a bit of anxiety for our eldest. She did *not* like the feeling of descending in the airplane.

We had a brief freak-out moment as the plane touched down, but this quickly turned to relief as we were now back on terra firma. I failed to explain that taxiing and waiting to deplane part, so we did endure some complaining about not getting off the airplane all that quickly.

We did end up with a dirty toddler diaper on the final part of the flight. I figured we could change this quickly before we got to customs. We had no such luck. As this was our kids’ formal entry into the U.S., the process took quite a while. Customs at Houston Hobby Airport is still worlds better than customs at George Bush Intercontinental. I’m thankful a 3-hour customs ordeal was *not* part of our first time flying with kids. We’ll have to save that for later (or get them all Global Entry).

The final part of our adventure included navigating security, chowing down some pizza, and then rushing to catch our connection to the Bay Area. Five hours later we touched down in California. I never thought I’d ever say I was happy to be back in Oakland.

Final thoughts

Overall, our first time flying with kids ended up going about as smoothly as I’d hoped. We prepped them pretty well, and it paid off. The older two thoroughly enjoyed the experience, and I’m certainly not afraid to take our toddler on another flight, either.

Most of all I hope that this means they’ll all quickly become great little travelers!

Crazy Deal! Get a Southwest Companion Pass after only one purchase!

For a limited time, California residents have access to a phenomenal deal. Southwest has an open offer to all California residents that allows them to earn the amazing Southwest Companion Pass after opening a new Southwest credit card and making a single purchase.

I’ve previously written about Southwest Airlines being my favorite airline  (honestly, this is not really true anymore, but they are pretty amazing). We’ve even leveraged the amazing Southwest cancellation policy for some recent bookings.

Targeted Southwest Companion Pass California offer

Last week there were reports of a targeted credit card offer being sent to *some* CA residents where they could earn a companion pass after only one purchase. The amazing news is that this is now being extended to all residents of California.

Here is the link to the personal Southwest Companion Pass California card offer. The welcome bonus also offers 40,000 points after spending $1,000 in the first 3 months.

Here is the link to the business Southwest Companion Pass California card offer. The welcome bonus also offers 60,000 points after spending $3,000 in the first 3 months.

(Neither of these are affiliate links)

Obviously, if you aren’t a resident of California, you won’t qualify for the Companion Pass offer.

Why the Companion Pass is *totally* worth getting

The Southwest Companion Pass is considered by many to be the “holy grail” of domestic (and some international) travel. It essentially gives you a 2 for 1 deal for both paid travel *and* award travel on Southwest airlines. It essentially doubles the value of all your Southwest RapidRewards points.

If you’re a traveling couple, you’ll only pay the points or fare for one person, plus the $5.60 TSA fee for both. If you’re a traveling family, you could fly 4 people for the price of 2 if *both* parents obtain a Southwest Companion Pass through this offer. This would be a mere $44.80 plus points for 2 tickets for a family of 4 round-trip anywhere in the U.S. Southwest flies! Talk about a phenomenal deal!

You can read up on the fine print of the Companion Pass here. But it honestly is as good as it sounds.

Southwest Companion Pass California offer targeted

Qualifying for the Southwest Companion Pass

Typically, you need to either fly 100(!) qualifying Southwest one-way segments in a year, or you need to accrue 110,000 qualifying points. Sound difficult? It certainly is for most people without a way to generate extra spending or without a business with significant expenses to charge. Here is the rundown on qualifying for the pass the traditional way.

The typical back door to getting the Southwest Companion Pass has been opening a new Southwest card and then spending the rest, or opening two Southwest cards in a year to meet, or nearly meet, the qualifying points requirement. The sign-up bonus for the card(s) counts toward the 110,000 point total needed.


If you’re interested in taking even a couple vacations next year, I guarantee that these offers will pay off the card fees required. Don’t pass up this Southwest Companion Pass California card offer!

Header image courtesy of BriYYZ under CC 2.0 license.

Leveraging the Southwest cancellation policy for adoption flights

My wife and I are now three weeks into an adoption trip of about 6 weeks in Costa Rica. We are thoroughly enjoying both our 3 kids and their beautiful country.

But it’s definitely a long trip. We can’t wait to head home and get things back to normal, albeit a new normal.

So I couldn’t keep myself from booking our tickets home. It may seem like it’s a bit early since we don’t know when we can come home yet. But with the stellar Southwest cancellation policy, there is no downside to booking now. I’ve actually leveraged their generous policy twice on this trip, so I figured I’d provide a rundown.

The fantastic Southwest cancellation policy

Southwest Airlines has one of the best cancellation policies I’ve ever encountered. Award tickets are completely refundable, up until just minutes before the flight. In a nutshell:

  • Tickets purchased with RapidRewards points are 100% refundable.
  • Tickets can be cancelled up to 10 minutes before the flight.
  • There is no cancellation fee!
  • Even if you “no show” your award ticket, your points are redeposited. Any taxes and fees will be added to your travel funds and usable toward future travel.

The Southwest cancellation policy for revenue tickets is good as well. Here everything depends on which fare type you purchased. For Wanna Get Away fares, the following applies:

  • Fares are non-refundable, but the funds will be saved and can be applied to purchase of future travel for the original ticketed passenger up to one year from the original flight date.
  • There is no cancellation fee!
  • In the event of a “no show”, the fare is forfeited. Note that if you can show up within 2 hours of your original flight time and still fly standby on the next flight as part of the unwritten “flat tire rule”.

Business Select and Anytime awards are completely refundable (or you can choose to keep the reusable travel funds). Even if you “no show” one of these tickets, your travel funds will be deposited in your account and will be usable for future travel.

Southwest cancellation policy - fare rules

Considering that many other airlines sell completely nonrefundable tickets or charge a hefty fee to refund a fare, Southwest’s policy is extremely generous.

Leveraging the policy on our way to Costa Rica

My wife and I flew to Costa Rica on one-way United award tickets. This allows us plenty of flexibility in deciding when to book tickets back. I *really* didn’t want to lock us into a date on United, since their change policy is so bad.

However, I failed to realize that Costa Rica requires proof of return flights. Oops. At the ticket kiosk in Houston we were given a final screen of “please see agent” rather than collecting our tickets. A United employee walked over and informed us that we had to have proof of return flights.

Southwest to the rescue. In only a few minutes I had award flights back to the U.S. booked on Southwest using my wife’s points. I didn’t really care that I’d only booked us back to Houston. We wouldn’t be using them anyway, and I cancelled them two days later. But it was enough to present to the agent and get us through check-in and onto our flight.

Do note that booking a ticket on another airline could have worked as well, but I would have had to cancel within the 24-hour refundable booking window.

Leveraging the Southwest cancellation policy for our return flights

Just a few weeks later I decided to lock in our return flights. By “lock in”, I simply mean locking in a good rate. The tickets are obviously 100% refundable under the Southwest cancellation policy.

Generally, our adoption agency doesn’t suggest that people book flights back until they have their final Visa appointment. This is obviously to save adoptive parents time and headache by avoiding tickets changes. But with the fantastic Southwest cancellation policy, there is no downside to booking now!

There was one more complication, however. Given that we aren’t 100% sure of what our children’s names will be on their passports, booking airfare is problematic. Name changes are typically not allowed.

I reached out to Southwest on Twitter and explained our adoption situation to them. An agent confirmed that we could change the names of the kids once we have their information. I sent our record locator over once I’d booked the tickets, and the agent added a note to our account. I was extremely happy Southwest was this gracious.

I also had to guesstimate our return date. I decided to play it safe and book a bit further out than we hoped to be here. Southwest also (sadly) doesn’t publish a SJO-HOU-OAK fare every day of the schedule, so I had to pick one of the few days this route is available.

If we do end up taking these flights, all five of us will fly home for 62,000 RapidRewards points and $290, which is a deal!

Be aware of the Southwest change policy!

Unlike the Southwest cancellation policy, the Southwest change policy is no longer as friendly as it once was. When changing a fare, you’ll be warned that the fare will become non-refundable! This kinda goes against the grain of the rest of Southwest’s policies, so make sure you keep this in mind.

If you still do want to change a ticket, you still won’t be charged a fee. Unlike most other airlines, change fees don’t fly with Southwest. You will still pay the difference in fare, if applicable.


The Southwest cancellation policy is definitely something to have in your back pocket. It has come in handy for us on multiple occasions, including twice on just this trip.

With Southwest, what’s not to LUV?

Featured image courtesy of BriYYZ under CC 2.0 license

A Beginner’s Rundown On Southwest RapidRewards

Southwest Airlines is one of my favorite airlines. Actually, I previously wrote about how they are my favorite airline, but I may need to qualify that now. They are my favorite domestic airline. Alaska is also giving them a run for their money. But Southwest sill reigns supreme due to their fantastic checked luggage allowance, great service, cheerful personnel, and tendency to arrive at destinations ahead of schedule. Honestly, I cannot remember the last time a was on a delayed Southwest flight.

While I could continue my unabashed monologue on the merits of Southwest, I want to instead focus on solely their loyalty program: RapidRewards.

Rapid Rewards Basics

Unlike the majority of airline loyalty programs, RapidRewards neither uses a currency of “miles” nor prices awards based on zone or distance. Instead, you earn RapidRewards points, and award prices are revenue-based (i.e. correlated with the price of cash fares). Zones don’t exist. If a cash fare is cheap, the price in points will be cheap. For example, a one-way flight from Oakland, California to San Diego, California costs either $69 or only 3,676 points.


Flights next month from OAK-SAN start at $69.

This award price is incredible. Other domestic carriers generally charge 7,500 to 12,500 miles for the same one-way ticket. This is because all are priced by zone and/or distance, and since the entire United States is one zone, it doesn’t matter if you are flying OAK-SAN or OAK-MIA. Same price. Some other carriers offer “short hop” prices for routes like OAK-SAN, but you should still expect to pay at least twice the points that Southwest requires for the Oakland-San Diego ticket. Nothing beats this value.


Or they start at 3,676 RapidRewards points plus $5.60 in government fees.

Revenue-based award pricing may seem like a boon, but it is a double-edged sword. During peak travel times, the price of paid fares usually goes through the roof, and so do award flight prices. This example of an Oakland-Baltimore flight the Sunday of Thanksgiving weekend is a perfect illustration. The cash fare is $405 one-way! Or you could instead pay 29,089 RapidRewards points. Any other carrier would charge you 12,500 miles if they had saver award space. But good luck finding availability!


OAK-BWI fare on 11/27/16. Or 29,089 RapidRewards points. Might be worth it in a pinch.

If you are dead set on a Thanksgiving visit with family, Southwest could still be your go-to in a pinch. As long as a seat is available, you can purchase it with points rather than cash. Even if the price is astronomical.

What Are Points Worth?

Which brings us to an important question: how much is a RapidRewards point worth? Well…it depends. Southwest’s award ticket prices are correlated to cash fares, but there isn’t a fixed value per point. You should expect to get about 1.5 cents per RapidRewards point, but it varies. Price, demand, route, and potentially other factors come into play. At least that is my deduction. The actual award pricing algorithm is a black box.

So we just have to roll with it. As I mentioned before, 1.5 cents per point is a decent baseline. In the OAK-SAN example above, the exact cash fare was $68.98. Subtracting the security fees and dividing by the award price of 3,676 points, we are left with a value of 1.72 cents per RapidRewards point. Not bad. This is on the high end. Conversely, the OAK-BWI Thanksgiving example is only a return of 1.37 cents per point.

From this we can surmise that high price and/or demand results in a worse return for your points. I have read complaints about Southwest not being forthright about their award pricing structure, or that the “black box” system allows them to change it incrementally without people noticing, but I don’t really buy this argument. Southwest is known for their great customer service, and a subtle devaluation would go completely against the grain of their organization. So it really doesn’t bug me that awards cost more during peak periods. I just accept it.

Earning Rapid Rewards Points

So now we know how awards are priced. But how do we earn RapidRewards points?

Well, there is the obvious: by flying Southwest. Depending on the fare class, you earn either 6x, 10x, or 12x the base fare. Business select fares earn the most while the “Wanna Get Away” fares earn the least.


Fare rules and RapidReward earning rates for Southwest’s 3 fare classes.

You may think that this means I would earn 414 points for the $69 OAK-SAN “Wanna Get Away” fare in the first example. In reality, I would only 306 points. This is because “base fare” is the price of the fare without any taxes or fees. It turns out that the base fare for that flight is only $51.05, so that’s where the total of 306 (51 x 6) RapidRewards points comes from. You can see the fare breakdown once you have selected a flight on southwest.com and moved to the Price/Summary page.


Sample fare breakdown for the OAK-SAN flight.

The “Wanna Get Away” fares are nearly always significantly cheaper than either the Business Select or Anytime fares, so there is no reason to pick the more expensive ones just for the points multiplier.

There are a number of ways you can earn RapidRewards points other than flying. Southwest has partnerships with a number of hotel chains and rental car companies, some of which offer a significant number of RapidRewards points. Hotel partners include Best Western, Choice Hotels, La Quinta, Marriott, Hyatt, and more. I do not advocate foregoing hotel points in order to earn RapidRewards points, unless you are staying with a chain that you rarely utilize. You can also transfer Marriott points to RapidRewards points.


Earn extra points with Southwest’s several car rental partners.

Car rental is another option. I only collect rental points with two providers (Hertz and Enterprise), so earning RapidRewards points for rentals with other companies can be a great deal. There is a “Frequent Flyer Surcharge” on most car rentals when you earn points, but it is on the order of $1 per day. Generally, it’s totally worth it.

Other means of accruing points include the RapidRewards shopping portal, the dining program, and various opinion and survey panels. I often use the dining program when I am traveling for work. It is a nice extra bonus. Figure out what works for you. The surveys can easily require more time than they are worth.

Finally, there are the co-branded Southwest Visa cards issued by Chase. They offer okay value. Try to apply when they are offering a sign-up bonus of 50,000 points. The cards both earn 2 points per dollar on Southwest flights and purchases made with Southwest’s hotel and rental car partners. For all other purchases you earn 1 point per dollar.

On the surface this seems like a pretty good deal. However, Southwest is a 1:1 transfer partner of Chase Ultimate Rewards, so the Chase Sapphire Preferred card offers the same (or better) earning potential, with added benefits like better purchase protection and trip insurance. Plus, your points aren’t locked into Southwest.

The disadvantage is that earning Chase points and transferring them to Southwest doesn’t help you earn the Companion Pass (more on this some other time). This is the primary advantage of the co-branded credit cards. Any points earned via credit card spending do count toward Companion Pass qualification. You can also earn Tier Qualifying Points (TQPs) with a large amount of spending (1,500 TQPs per $10,000 in spending, up to a total of $100,000) which helps toward A-List qualification. The credit cards also offer anniversary points that help offset the annual fee.

Using Rapid Rewards Points

This is the easy (and fun) part. Booking flights using RapidRewards points at southwest.com is really straightforward. When you search for flights, you can toggle between dollars and points. Simply choose the price(s) in points, and click continue. You’ll then see the total points required and the fees you’ll still have to pay. When you complete checkout, the points will be immediately deducted from your total balance.


Total cost in cash and points for the OAK-SAN award fare.

What if you need to change or cancel the award flight you just booked? This is where Southwest really shines. Unlike most carriers that charge ridiculous fees for award ticket changes or cancellations, Southwest allows you to cancel award flights free of charge up until 10 minutes before your flight! The fees will be refunded, and your points will be redeposited. That’s awesome.

You can also use this fantastic cancellation/change policy to save points. Say I booked the OAK-SAN flight for 3,676 points yesterday, but the price dropped to 3,056 points today. Rather than keep the ticket I booked yesterday, I could simply cancel it and re-book the same flight at a lower cost. Voila, I saved 620 points! This “trick” has come in handy on several occasions.

Some Final Thoughts

So there you have it. I hope you have enjoyed this rundown on Southwest RapidRewards. It is a fantastic program and offers great value for domestic (and a few international) flights. If you haven’t already, enroll for a free RapidRewards account and start earning points. Consider getting a Chase Sapphire Preferred card to boost your balance. Above all, LUV Southwest.

Header image courtesy of BriYYZ.

A Mostly Empty Southwest Flight? What?

Southwest is my favorite U.S. airline, offering reasonably priced fares, consistent service, and more ticketing flexibility than any other airline I have ever flown. It is no surprise to me that nearly every Southwest flight I have ever taken has been completely full.


Until the most recent one. There were maybe 40 people on the entire 737. So strange. We had rows and rows of empty space around us. I guess this must happen now and then, but after 12+ legs on Southwest, I was beginning to think that they were always full. If the flight had been more than 50 minutes, I probably would have laid down across a row and taken a nap.

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