How 100,000 Southwest bonus points got me an all-inclusive trip to Mexico and a Companion Pass

Oct 21, 2021

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Editor’s note: Chase provided the author with 100,000 Southwest points for use on this trip. The opinions expressed below are entirely hers and weren’t subject to review by Chase or Southwest.


How would you use 100,000 Southwest points on a fantastic trip? That’s the question TPG posed to three staff members with Southwest credit cards back in July.

And that’s the question you might be asking yourself now, thanks to the new up to 100,000-point sign-up bonuses available on several Southwest credit cards.

Usually, posts by TPG staff on how they’d spend a set number of points or miles are purely theoretical. But for me, this assignment involved real points and an actual vacation.

Typically, I dole out just a few thousand Southwest points per flight – attractive award pricing is one of the reasons I like the airline’s Rapid Rewards program so much. But this challenge required me to deviate from my typical redemption pattern. Since I had to redeem 100,000 Southwest points on just one or two amazing trips of my choosing for this assignment, I decided to have some fun.

Snag a sign-up bonus of up to 100,000 bonus Southwest Rewards when you apply for the following cards using these application links:

Each card currently offers new cardholders 50,000 points after they spend $2,000 on purchases in the first three months from account opening. Plus, they can earn 50,000 more points after spending $12,000 on purchases in the first 12 months from account opening.

Luckily, I remembered that Southwest credit cardholders can redeem Southwest points not just for flights with the airline, but also for gift cards, hotel stays, and even some international flights to destinations not served by Southwest through the More Rewards travel program.

That’s how I decided to redeem these 100,000 Southwest points on a vacation for two to Mexico. This redemption included not only Southwest-operated flights but also three nights at an all-inclusive resort. It was just the sort of last-minute beach getaway I needed before the winter holidays arrive.

Oh, and because of the 100,000-point bonus, I picked up the Southwest Companion Pass along the way. Here’s what I did – and how you can tweak this approach to plan the trip of your dreams too.

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In This Post

How I used 100,000 Southwest points on a vacation

I redeemed just under 100,000 Southwest points to book a three-night vacation for two to Riviera Maya, Mexico, including flights and an all-inclusive stay.

Earning 100,000 Southwest points this year put me over the top for a Companion Pass (more on that below). So, I only needed points to cover my own flights since I could bring a companion along after paying just the taxes and fees on their ticket.

Here’s how my redemption tallied up:

  • 12,865 points plus $70.54 in taxes and fees: Southwest flights from New York-LGA to Cancun via St. Louis for two passengers
    • 12,865 points plus $35.32 in taxes and fees for me
    • 0 points plus $35.22 in taxes and fees for my companion
  • 65,395 points plus $4 in local fees: Three nights at Iberostar Paraiso Del Mar All Inclusive in a junior suite for two guests
  • 20,501 points plus $114.46 in taxes and fees: Southwest flights from Cancun to Atlanta via Denver for two passengers
    • 20,501 points plus $57.23 in taxes and fees for me
    • 0 points plus $57.23 in taxes and fees for my companion

These are easily the most expensive Southwest flights I’ve ever booked, which tells you what a good deal Southwest award redemptions typically are. Flights would have been less costly if I’d booked earlier or had flexible dates or destinations. But since I had a small travel window between commitments, I didn’t have much date flexibility. Plus, these weren’t terrible rates for two passengers thanks to my Companion Pass.

After searching hotels through More Rewards in many destinations, resorts in the Cancun area provided the best value on my dates.

So, I went for it.

Related: 10 easy ways to earn more Southwest Rapid Rewards points

Using points for Southwest flights to Mexico

Routing for my two Southwest bookings
(Screenshot courtesy of gcmap.com.)

In total, I redeemed 33,366 Southwest points and paid $185 in taxes and fees for flights to and from Mexico for my husband and myself. Unfortunately, the expensive taxes and fees on flights into and out of Cancun added a significant cash outlay to our award trip – but at least we saved on the airfare by using points and the Companion Pass.

Booking Southwest award flights

I needed to depart New York City on Oct. 7, 2021, so one Southwest flight stood out as best in terms of award cost:

(Screenshot courtesy of southwest.com.)

I reserved the eight-hour itinerary connecting in St. Louis for 12,865 points plus $35.32. I added my companion a few weeks later for $35.22. I waited to add him because you can’t reprice your flight to a lower fare when a companion is attached, whereas I could still add him as long as there were empty seats on my flights.

Adding a companion to a flight
(Screenshot courtesy of southwest.com.)

After deciding to book a three-night all-inclusive stay in the Cancun area, I needed to find a departure back to the U.S. on Oct. 10, 2021. Unfortunately, Sunday departures from Cancun are often pricey, and this Sunday was no exception.

Southwest calendar of fares
The calendar of fares between Cancun and Atlanta a few days before the price dropped slightly and I booked. (Screenshot courtesy of southwest.com.)

Usually, I would have redeemed a few hotel free night certificates to extend my stay at a different hotel in Cancun. But for the sake of just seeing how far 100,000 points could get me on this project, I chose the cheapest Southwest award flight from Cancun to Atlanta on Oct. 10, 2021:

Southwest fares from Cancun to Atlanta
(Screenshot courtesy of southwest.com.)

As the flight approached and it became clear I wouldn’t be able to change to a less expensive award, I added my companion to this itinerary as well.

Related: Why I’ll never book Southwest flights with Chase points the same way again

Flying Southwest to and from Cancun

When our departure day from New York arrived, I was impressed by the new LaGuardia terminal and surprised by the calm Southwest check-in area. Our first Southwest flight from New York-LGA to St. Louis was about 50% full and we were each able to get an entire row to ourselves near the back of the aircraft. After all, Southwest allows you to choose your own seats instead of pre-assigning specific seats.

On the other hand, there were only five empty seats on our Southwest flight from St. Louis to Cancun. We sat near the front of the aircraft so we could reach immigration ahead of other passengers from our flight. This strategy worked well, as the immigration lines grew longer once we were already in them as arriving passengers from multiple flights created a bottleneck.

For the return, our Southwest flight from Cancun to Denver had just a few open seats, potentially due to Southwest’s operational meltdown that happened that same weekend. However, the flight arrived in Denver approximately on time, so our plans were unaffected.

Once in Denver, we used Global Entry to clear immigration and then TSA PreCheck and Clear to get back through security quickly.

Service onboard Southwest was mostly light-hearted, as I’ve come to expect from the airline. In-flight drink service is still limited to a choice of five drinks and passengers are interestingly asked to order non-verbally by holding up a certain number of fingers to indicate their drink option. But otherwise, the airline’s cheerful ambiance seems to have weathered the pandemic.

Related: Cool places you didn’t know you could fly on Southwest

Using Southwest points for an all-inclusive resort stay

Southwest credit cardholders can redeem Southwest points for more than just Southwest flights through the More Rewards program. However, note that Rapid Rewards members without a Southwest credit card can’t use the More Rewards program.

Cardholders can use More Rewards to redeem Southwest points for international flights with other carriers, gift cards, hotels, rental cars and more. (The More Rewards program portal has been down sporadically recently, including at the time of writing, but it was functioning properly during my travel planning process.)

The redemption rates through the More Rewards program are typically lower than you can get when redeeming for Southwest flights – especially if you have the Companion Pass. But, I still had 66,634 Southwest points left after booking flights to and from Cancun. So, I looked for the best value well-rated hotel I could book through the More Rewards program. After all, my mission was to book a vacation with 100,000 points.

Booking an all-inclusive stay through More Rewards

There are all manners of hotels bookable, including all-inclusive resorts, through Southwest’s More Rewards program. You can start by logging into your Southwest account in one browser window. Then, open a new window and go to the More Rewards home page.

Southwest More Rewards
(Screenshot courtesy of awardhq.com.)

Click on “Explore Rewards” to see what you can book through the More Rewards program. If you want to book a hotel or resort stay using Southwest points, click on “Hotel and Resort Stay” under the “Travel” dropdown.

Book travel through Southwest More Rewards
(Screenshot courtesy of awardhq.com.)

Then, enter the details of your hotel stay, including dates and destination, to search. You may need to explore by specific cities in some general destinations. For example, I found the Iberostar resort when I searched Puerto Morelos instead of Cancun.

Especially if you’re booking an all-inclusive resort or a resort that charges by person, be sure to search using the correct number of adults and children.

Book a hotel through Southwest More Rewards
(Screenshot courtesy of awardhq.com.)

Once you get results, you can sort and filter them.

Book a hotel through Southwest More Rewards
(Screenshot courtesy of awardhq.com.)

When I filtered by all-inclusive properties, I got the following 28 hotels sorted from least expensive to most. Then I searched for reviews of the least expensive properties to determine whether any would provide an overall better experience than the others.

Book a hotel through Southwest More Rewards
(Screenshot courtesy of awardhq.com)

In the end, I decided on the Iberostar Paraiso Del Mar All Inclusive, which is part of the larger five-resort Iberostar complex south of Cancun.

Book a hotel through Southwest More Rewards
(Screenshot courtesy of awardhq.com.)

A junior suite was available for just 1,434 more points per night over the cost of a standard room. Even though the junior suite didn’t that look much better than the standard room in photos, I went for it since I had a few points to spare.

Book a hotel through Southwest More Rewards
(Screenshot courtesy of awardhq.com.)

As mentioned, the redemption rate for three nights in a junior suite with two adults came to 65,395 points.

Book a hotel through Southwest More Rewards
(Screenshot courtesy of awardhq.com.)

Based on TPG’s valuations, 65,395 Southwest points are worth about $981. However, I could have booked the same three-night stay in a junior suite on Iberostar’s website for $732. As such, I got about 1.12 cents per point on this redemption, which is higher than you’ll typically get when redeeming through the More Rewards program, but lower than you’ll get when redeeming for Southwest flights.

Related: The zero-cost vacation: 100+ all-inclusive resorts you can book with points

Staying at Iberostar Paraiso Del Mar All Inclusive

A few summers ago, I lived at an all-inclusive resort in the Dominican Republic for almost a month. I expected my stay at the Iberostar Paraiso Del Mar All Inclusive would be similar in experience and quality.

When we got out of the taxi at the reception area, I was delighted to realize this stay would likely be much better.

In short, the vast open-air lobby and flamingos in a nearby pond provided an excellent first impression. Before I even completed checking in, a staff member had already brought me a welcome drink.

There was plenty for me to do at the resort before even considering any excursions.

I loved joining a pool volleyball game, playing ping pong by the pool and participating in a water aerobics class. I also enjoyed hanging out in the activity pool, which had music all day, activities every few hours and even a swim-up bar. As a casual drinker, I found the drink quality and selection perfectly acceptable. Best of all, I wasn’t spending any real cash for my drinks and food since it was all booked with Southwest points.

The dining options were solid overall. Although a three-night stay only comes with one dinner reservation, we were able to snag an extra one by asking for a same-day dinner reservation on our second day. We ended up with reservations for the resort’s Brazilian restaurant and Japanese restaurant.

The Brazilian restaurant was fun because waiters visited each table with skewers of different meats that they could slice to order.

But, I enjoyed the Japanese hibachi restaurant even more. This one had an interactive cooking demonstration and a wide variety of foods on offer.

You can also eat at the poolside buffets for lunch or walk over to a taco shop in the shopping center shared by all five Iberostar resorts in the complex. The poolside buffets are convenient, but I highly recommend the stroll over to the taco shop to enjoy its made-to-order tacos and drinks. The al pastor tacos and shrimp quesadillas were delicious.

There’s also a coffee shop and crepe shop in the shopping center area. The coffee shop is an excellent alternative if you want a quicker breakfast than the buffet restaurant can provide. Its tres leches cake was on point.

I appreciated that this Iberostar resort used reuseable cups, bottles and plates when possible. For example, bartenders served drinks at the pool bars in reusable plastic cups, and you could refill glass water bottles via dispensers in each lodging building.

Finally, I should mention a little about my room. I’d booked a junior suite, which I knew from pictures was simply a slightly larger room than the standard – but I figured it was still worth the extra points. It may have been worth a few extra points, but in general, the room decor and some of the other hotel facilities felt outdated. That’s probably to be expected after the COVID travel slump, especially considering I picked the least expensive resort in the five-resort complex. But, as tourism picks back up, I hope Iberostar invests in a property refresh.

That said, my room was clean and functional, and the air-conditioning worked fabulously. But I wouldn’t recommend this resort if you want fancy accommodations or plan to spend a large portion of your non-sleeping time in the room.

Related: 13 mistakes to avoid at all-inclusive resorts

Earning a Southwest companion pass

I didn’t initially think I’d receive a Southwest Companion Pass as part of this project. But, when the 100,000 Southwest points arrived in my Southwest account, I was thrilled to see that it had put me over the top for a Companion Pass that is valid through the end of 2022. This would also happen if I had earned the 100,000 points as a sign-up bonus on one of the Southwest credit cards.

And, although I enjoyed my trip to Mexico, I expect the Companion Pass will provide me with even more value through the end of 2022.

Southwest Companion Pass basics

Boarding a Southwest plane
Bring your companion with you on flights for just the taxes and fees with a Companion Pass. (Photo by Summer Hull/The Points Guy.)

In short, the Southwest’s Companion Pass is an extremely valuable perk. When you have a Companion Pass, one person you select can fly with you every time you purchase or redeem points for a Southwest flight. All you have to do is pay the taxes and fees on their fare. And although you can only designate one specific person as your companion, you can change this person up to three times each calendar year.

Normally, you must fly 100 qualifying one-way flights or earn 125,000 Companion Pass qualifying points in a calendar year to earn a Southwest Companion Pass. But, once you meet one of these requirements, you’ll earn the Companion Pass for the rest of the current year as well as for the following calendar year.

Related: 13 lessons from 13 years’ worth of Southwest Companion Passes

Leverage Southwest credit card bonuses for a Companion Pass through 2023

Currently, several consumer Southwest credit cards offer the ability to earn up to 100,000 Rapid Rewards points after you spend $12,000 in the first year. In particular, new cardholders can earn 50,000 points after spending $2,000 in three months from account opening and 50,000 more points after spending $12,000 in 12 months from account opening with the following cards:

Especially since these cards offer a two-tier bonus, it’s important to carefully time when you earn both parts of the bonus if you want to earn a Companion Pass for the maximum time possible. After all, Southwest’s website notes:

Points earned during a billing cycle on a Southwest Rapid Rewards Credit Card from Chase are not available for redemption or qualification for Companion Pass status until they are posted on your billing statement and posted to your Rapid Rewards account. Only points posted on your billing statements and posted to your Rapid Rewards account during the same calendar year are available for qualification for Companion Pass status.

You could earn both tiers of the bonus quickly before the end of 2021. After all, since Southwest gave members 25,000 Companion Pass qualifying points this year to effectively reduce qualification requirements, you could earn the Companion Pass outright like I did even if you haven’t flown Southwest at all this year.

However, this is a risky strategy, since you’d need the sign-up bonus points to post to your billing statement and Rapid Rewards account by the end of the year. Instead, I’d recommend trying to earn both tiers of these cards’ bonuses in early 2022 and then using your spending and any other Companion Pass-qualifying activity to earn the pass as quickly as possible next year. That way, the Companion Pass you’d earn would be valid through the end of 2023 — up to nearly two years in all.

Related: The best credit card pairings to earn the Southwest Companion Pass

Bottom line

It was great to get a vacation with flights, lodging and food for two for just $310 out of pocket.

We didn’t incur any drink or dining costs and the resort even offered complimentary COVID testing for return to the U.S. Our only costs not covered by points were transportation between the airport and resort, the taxes and fees on our tickets, local fees on lodging and tips.

Redeeming 100,000 Southwest points in a completely different manner than usual was a fun exercise. But, although I enjoyed my trip down to Mexico, I wouldn’t necessarily recommend that most travelers redeem 100,000 points exactly as I did for this project.

After all, TPG values the 98,761 Southwest points I redeemed at $1,481. And, especially if you earn a Companion Pass, you’ll get much more value from your Southwest points when you redeem for Southwest flights (and use hotel points or cash to book lodging). Still, this was a fun exercise to see all the different ways the Southwest points you can get from just one card bonus could come in handy for a last-minute vacation.

After all, as TPG’s Andrea Rotondo noted a few years ago, miles and points valuations shouldn’t rule your world since points and miles are a bad long-term investment.

With that in mind, especially if you’re short on cash or have plenty of points, redeeming at a reduced redemption rate through the More Rewards program for a hotel stay may still be the right choice for you. Of course, picking up the Companion Pass along the way is just the cherry on top of strawberry daiquiri served at the swim-up bar.

Featured image by Katie Genter/The Points Guy.

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Editorial Disclaimer: Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, airlines or hotel chain, and have not been reviewed, approved or otherwise endorsed by any of these entities.

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