Finally reunited: How 100,000 Southwest points are taking me home for the holidays

Oct 25, 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.

I grew up in St. Louis mostly flying Southwest Airlines out of Lambert International Airport (STL). To this day, Southwest is still my main airline thanks to its customer-friendly policies, including allowing each passenger to check two bags for free and to change or cancel their tickets ahead of time without penalties.

That’s not to mention its affordable fares between my hometown and the East Coast, where I live now, making it easy for me to visit friends and family frequently. At least during normal times.

So earlier this fall, when TPG presented three staffers with the opportunity to map out trips using 100,000 Southwest points, my hand shot right up. Here’s how those points are helping me plan a holiday reunion with my family after COVID-19 kept us apart for much of 2020 and 2021, including last year’s holiday season.

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My first Southwest Rapid Rewards Card has seen better days. (Photo by Caroline Tanner/The Points Guy)

100,000 Southwest Points

If you’re wondering how we came to the 100,000-point mark, it’s because all three of Southwest’s cobranded personal credit cards with Chase are currently offering up to 100,000 points as part of their sign-up bonuses. As a reminder, those cards are:

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.

The three cards have also added new earning rates and benefits. I’ve had the Southwest Rapid Rewards Premier card for several years now, and it has just upped its earning rates to 3x on Southwest flights (it was previously 2x) and added new 2x earning rates on local transit and commuting purchases, including rideshares, as well as on internet, cable, phone services and select streaming purchases. It continues to earn 2x on Rapid Rewards hotel and car rental partners and 1x on everything else. Another new perk? Two EarlyBird check-ins every card anniversary that should help me snag those coveted window seats faster.

Meanwhile, here’s how I’m planning to put my 100,000 Southwest points to use this holiday season.

Meet me in St. Louis …

Although I’ve usually stayed on the East Coast for Thanksgiving since moving here in 2014, this year feels different. I was particularly eager to go home for this Thanksgiving family gathering after not seeing my parents for a whole year due to COVID-19.

Knowing I had a stash of Southwest points to rely on — especially since the airline doesn’t impose holiday blackout dates — made it easier to take the leap and lock in the flights.

I found plenty of excellent nonstop options from my current main airport, Ronald Reagan Washington National Airport (DCA), to St. Louis on Nov. 18. For the sake of a mostly uninterrupted workday, I chose the first one at 8:35 a.m. Because I will be flying to the West Coast for work the first week of December, I booked a one-way ticket … and it didn’t put much of a dent in my points balance, so there would be plenty left over to plan for the rest of my holiday travel.

(Screenshot courtesy of Southwest Airlines)

Now I get to look forward to being home for Thanksgiving for the first time in three years, which is a pretty great feeling.

Of course, everyone does the holidays differently, but for us, in certain years the three of us just spend the day at home together and order most of the meal from our local butcher since (family secret!) neither of my parents cook. That said, in order to keep things a bit healthier for us, I whip up my specialty dairy-free mashed potatoes and gluten-free stuffing … plus toss a salad on the table for good measure. If I’m being really honest, we always order a second batch of stuffing from LeGrand’s Market, too.

On the Thanksgivings when we do venture out, it will be to my Aunt Joan’s house to celebrate with my uncle and cousin, where we will no doubt hover around the kitchen while she cooks and look in awe at how she manages to do it all.

Get ready for some impromptu taste tests, Aunt Joan!

I’ll be home for Christmas

Perhaps more so than Thanksgiving, I am beyond thrilled to be going home for Christmas. Since I was being cautious during the COVID-19 surge last December, it was the first time I’d ever spent Christmas away from my family.

But it’s not just being with my family I’m excited about. As a family Christmas present, I hoped to use points to tack on a trip to Chicago with my parents between Thanksgiving and Christmas since it’s our favorite city and we spent a lot of time there while I was growing up.

Some of our favorite activities include taking an architectural boat tour along the Chicago River, going to a Cubs or Sox game and proudly sporting our Cardinals gear (IYKYK), walking along the Magnificent Mile and visiting the Merchandise Mart. Among the places we frequent when our bellies start to rumble are Eataly, Gino’s East for pizza (no deep dish for me), Chinatown, Greek Islands, Shaw’s Crab House and Fish Bar in Lakeview, my own personal fave.

My dad and I at a bar in River North in 2018. (Photo by Caroline Tanner/The Points Guy)

I plan to fly from Washington, D.C., while my parents will make their way from St. Louis to meet me at Chicago Midway International Airport (MDW). There were plenty of nonstop options available for me to fly to Chicago on Dec. 9, and I chose the 9:35 a.m. option to arrive shortly before my parents for less than 5,000 Southwest Rapid Rewards points.

(Screenshot courtesy of Southwest Airlines)

My parents had two options departing from St. Louis and they chose the 10:50 a.m. departure at less than 7,000 points per ticket.

Related: ‘Flat out not true’: Incoming Southwest CEO denies pilot walkout rumors to TPG

(Screenshot courtesy of Southwest Airlines)

Going back to St. Louis on Dec. 12, there were three nonstop flights for the three of us to select from. The 9:30 a.m. flight seemed most suitable and would get us back in time to enjoy the day together at home. Three tickets on that flight ring in at just under 21,000 total points.

(Screenshot courtesy of Southwest Airlines)

Before starting to plan my trips, I had almost forgotten that Southwest cobranded credit card holders can also use their Rapid Rewards points to book hotels, among other options, through the program’s More Rewards portal.

That said, it’s not a particularly great value, and navigating the website isn’t always intuitive. But I figured it couldn’t hurt to take a look.

 Related: Celebrating 50, Southwest and Disney unveil new livery; we have some thoughts

(Screenshot courtesy of Southwest Airlines)

In order to use your Rapid Rewards points to book hotels, you first must log in to your Southwest account as usual in one window.

Next, open up the “Redeem More Rewards” page in a new window. If you get an error, make sure you are logged in from the other window. If the page loads, log in to your account on the right-hand side. Again, two windows must be open at this point; different tabs will not suffice.

Look for the “Redeem for More Rewards” on the right side of the main window and click on the yellow button underneath that says ‘”Explore Rewards.” At this point, the page should load and you would hover over “Travel” (under check-out) near the top of the page and then click “Hotel and Resort Stay.”

Unfortunately, the Southwest site was “down for maintenance” when I wrote this story. Mercury was in retrograde, after all. But I had looked up options earlier in October, when I was doing all my planning.

(Screenshot courtesy of Southwest Airlines)

Under normal circumstances, however, the final step would be to let the page load and then you should be able to do a search that will show prices in points. Ironically, I also received an error message in attempting to determine the points value for a Southwest rental car redemption in September.

In order to decide whether a booking like this is a worthwhile use of Rapid Rewards points, divide the cash price of a stay by the number of points you’d have to redeem, and then multiply by 100. If that amount is less than the 1.5 cents per point that TPG’s monthly valuations peg Southwest Rapid Rewards points at, it’s probably best to avoid.

At the time I first conducted my test search for hotels to stay at Dec. 9-12, I was left with only three options:

  • River Hotel for 54,041 points or $451 — yielding a value of 0.8 cents per point.
  • Club Quarters Hotel, Wacker at Michigan for 54,041 points or $441 — yielding a value of 0.8 cents per point.
  • Central Loop Hotel for 57,375 points or $422 — yielding a value of 0.7 cents per point.

None of these seemed like a great option, so I decided just to book a paid stay instead. That, in turn, was a way to earn even more Rapid Rewards points. For example, a room with two queen beds at the Hyatt Centric on Michigan Avenue for three nights would have cost $531, but also earn me another 18,000 Rapid Rewards points. That said, I’d probably book this particular option directly with Hyatt in order to earn World of Hyatt points as well as credit toward elite status … but 18,000 Rapid Rewards points is not too shabby.

(Screenshot courtesy of Southwest Airlines)

Read more: How to redeem points with the Southwest Rapid Rewards program

Going back to D.C. after the holidays, my mother pointed out that finding an Uber on New Year’s Eve is likely to be much more of an ordeal than on the Dec. 30, which ultimately led me to book a flight back to Washington on the 30th, departing at 8:35 a.m.

If you’re sensing a theme by now, I tend to prefer taking the first nonstop flight of the day as less is likely to go wrong in terms of scheduling in the mornings than by the time a whole day of flights has operated.

(Screenshot courtesy of Southwest Airlines)

Final trip cost

Adding up the points for all three trips — going home for Thanksgiving and a weekend trip to Chicago before heading back home for Christmas — all the flights for my parents and myself would total just 51,088 Rapid Rewards points. That’s pretty amazing if you think about it.

With a 100,000-point bonus to work with, that leaves nearly 49,000 points. I could have used them to offset a hotel in Chicago, but ultimately am going to hang on to them for future flights where I’ll get more value. In particular, I’m considering something I’ve been putting off during the pandemic … a beach vacation in Hawaii, where Southwest has been ramping up its service and offering cheap fares.

One of the reasons I’m also comfortable holding some Southwest points back for now is the flexibility of the airline’s change and cancellation policies.

If I end up not being able to take any of these trips — due to any number of factors, including another potential COVID-19 surge — I will be able to get them back in my account and use them to see my family another time. Heck, maybe I’ll even bring my parents along with me to Hawaii.

My mother has always wanted to go, and I should be able to use points for a mother-daughter trip since the 100,000 points I earned were enough to put me over the threshold for a Companion Pass and the two-for-one travel it unlocks.

Bottom line

Points and miles aren’t my main beat at TPG, as I typically cover the news of the day. However, the opportunity to think of creative ways to redeem Southwest points and reunite with my family for the holidays to boot was too good to pass up. Beyond the simple valuation calculations we do for points, I reflected on how much more (albeit sentimental) value I would get from redeeming points to simply head home for the holidays.

That’s always a special trip, but it takes on an even sweeter taste this year after the time we’ve spent apart.

My family at my Northwestern graduation in 2018 in Evanston, Illinois. (Photo by Caroline Tanner/The Points Guy)

I’ve been counting down the days until I get back to St. Louis and my family makes our usual trip to see Christmas lights in Candy Cane Lane, walks around Forest Park, watches a variety of Lifetime holiday movies and “House Hunters,” orders thin-crust pizza and dines on The Hill at some of the city’s best Italian restaurants.

Since I work from home, I am lucky to have the option of spending a significant period of quality time in a location other than my own apartment. For me, there’s no way I would rather spend this time than with my mom and dad, as I haven’t had this much time with them since holiday breaks in college.

As we all get older, I appreciate this even more, along with the fact that I can use Southwest points virtually penalty-free in case I need to change or cancel plans. It’s all part of the reason why my family has remained loyal Southwest Rapid Rewards Premier Credit Card members all these years. In fact, my father still refuses to fly anywhere Southwest doesn’t operate and, while that’s not the case for me, I love him for that.

Featured photo by Steven M. Keller courtesy of Southwest Airlines.

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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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