Reunited at last: How 100,000 Southwest points are bringing me home for the holidays

Having grown up in St. Louis and primarily flying with Southwest Airlines from Lambert International Airport (STL), I still consider Southwest my go-to airline. Their customer-friendly policies, like allowing two free checked bags and no penalty for ticket changes or cancellations, keep me loyal.

Not to mention, their budget-friendly fares between my hometown and the East Coast, where I currently reside, make it easy for me to visit family and friends regularly—well, at least during typical times.

So, when TPG offered three staff members the chance to plan trips using 100,000 Southwest points earlier this fall, I eagerly raised my hand. Here's how those points are facilitating a long-awaited holiday gathering with my family after COVID-19 kept us apart for much of 2020 and 2021, including last year's holiday season.

100,000 Southwest Points

Curious about how we reached the impressive 100,000-point threshold? It’s because all three of Southwest's cobranded personal credit cards with Chase are currently offering sign-up bonuses of up to 100,000 points. Here’s a quick reminder of those cards:

• Southwest Rapid Rewards Premier Credit Card
• Southwest Rapid Rewards Plus Credit Card
• Southwest Rapid Rewards Priority Credit Card

Each of these cards currently provides new cardholders with 50,000 points after spending $2,000 within the first three months of account opening. Additionally, you can earn another 50,000 points by spending $12,000 in the first year.

The three cards have introduced enhanced earning rates and benefits. I’ve held the Southwest Rapid Rewards Premier card for several years, and it recently increased its earning rate to 3x on Southwest flights (up from 2x) and added a new 2x earning rate on local transit and commuting expenses, including rideshares, as well as on internet, cable, phone services, and select streaming subscriptions. It still earns 2x on Rapid Rewards hotel and car rental partners and 1x on all other purchases. Plus, there's a new benefit: two EarlyBird check-ins each card anniversary, which should help me secure those coveted window seats more easily.

Here's my plan for using my 100,000 Southwest points this holiday season.

Meet me in St. Louis ...

While I’ve typically spent Thanksgiving on the East Coast since moving here in 2014, this year is different. I’m especially excited to return home for this Thanksgiving gathering after being apart from my parents for a whole year due to COVID-19.

Having a reserve of Southwest points to draw from—especially since the airline has no holiday blackout dates—made it much easier for me to book my flights without hesitation.

I discovered numerous great nonstop flights from my current home base, Ronald Reagan Washington National Airport (DCA), to St. Louis on Nov. 18. To ensure a mostly smooth workday, I opted for the earliest flight at 8:35 a.m. Since I’ll be traveling to the West Coast for work in the first week of December, I booked a one-way ticket ... and it barely made a dent in my points balance, leaving me with plenty for the rest of my holiday travels.

I’m thrilled to finally be heading home for Thanksgiving after three long years, and it feels amazing.

Everyone has their own holiday traditions, but for us, some years we simply spend the day together at home, ordering most of our meal from our local butcher since (family secret!) neither of my parents cooks. To keep things a bit healthier, I prepare my signature dairy-free mashed potatoes and gluten-free stuffing ... and I always add a salad for good measure. Honestly, we usually end up ordering a second batch of stuffing from LeGrand's Market as well.

On the Thanksgivings when we do go out, it’s to my Aunt Joan's house, where we celebrate with my uncle and cousin. We’ll definitely find ourselves gathered around the kitchen, marveling at how she manages to handle everything.

Get ready for some spontaneous taste tests, Aunt Joan!

I’ll be home for Christmas

More than Thanksgiving, I can hardly contain my excitement about returning home for Christmas. Last December, due to the COVID-19 surge, I experienced my first Christmas away from my family, and it was tough.

But it’s not just the joy of being with my family that excites me. As a special Christmas gift, I plan to use points for a trip to Chicago with my parents between Thanksgiving and Christmas, our favorite city where we spent countless hours during my childhood.

Some of our beloved activities include taking an architectural boat tour on the Chicago River, catching a Cubs or Sox game while proudly donning our Cardinals gear (IYKYK), strolling along the Magnificent Mile, and visiting the Merchandise Mart. When hunger strikes, we love dining at Eataly, grabbing pizza at Gino's East (definitely not deep dish for me), exploring Chinatown, enjoying Greek Islands, and indulging at Shaw's Crab House and Fish Bar in Lakeview, my personal favorite.

I’ll be flying out from Washington, D.C., while my parents will be traveling from St. Louis to meet me at Chicago Midway International Airport (MDW). There were many nonstop flights available for my trip to Chicago on Dec. 9, and I selected the 9:35 a.m. option so I could arrive just before my parents, all for under 5,000 Southwest Rapid Rewards points.

My parents had two flight options from St. Louis, and they opted for the 10:50 a.m. departure at just under 7,000 points per ticket.

For our return to St. Louis on Dec. 12, we had three nonstop flights to choose from. The 9:30 a.m. flight looked like the best option, allowing us to enjoy the day together at home. The total for three tickets on that flight came to just under 21,000 points.

Before I began planning my trips, I nearly overlooked the fact that Southwest cobranded credit card holders can use their Rapid Rewards points for hotel bookings and other options through the More Rewards portal.

However, it’s not particularly cost-effective, and the website can be a bit tricky to navigate. Still, I thought it might be worth checking out.

To use your Rapid Rewards points for hotel reservations, you need to log into your Southwest account as you normally would in one browser window.

Next, launch the "Redeem More Rewards" page in a new window. If you encounter an error, ensure that you are logged into the other window. Once the page loads, log in to your account on the right side. Remember, you need to have two separate windows open; using different tabs won't work.

On the right side of the main window, locate the "Redeem for More Rewards" section and click the yellow button labeled '"Explore Rewards." The page should load, and you can then hover over "Travel" (under check-out) at the top, followed by clicking on "Hotel and Resort Stay."

Unfortunately, when I wrote this article, the Southwest website was experiencing "maintenance issues." It was, after all, during Mercury retrograde. However, I had explored options earlier in October while planning my trip.

Typically, the final step would involve letting the page load, allowing you to conduct a search that reveals prices in points. Ironically, I also encountered an error while trying to check the points value for a Southwest rental car redemption back in September.

To determine if a booking is a smart use of Rapid Rewards points, calculate the cash price of your stay divided by the points required for redemption, then multiply that figure by 100. If the result is below the 1.5 cents per point that TPG's monthly valuations suggest for Southwest Rapid Rewards points, it's likely best to pass.

When I first searched for hotels available from December 9-12, I found only three options remaining:

• River Hotel for 54,041 points or $451 -- offering a value of 0.8 cents per point.
• Club Quarters Hotel, Wacker at Michigan for 54,041 points or $441 -- also at 0.8 cents per point.
• Central Loop Hotel for 57,375 points or $422 -- which equates to 0.7 cents per point.

None of these options seemed appealing, so I opted for a paid stay instead, which would help me earn even more Rapid Rewards points. For instance, a three-night stay in a room with two queen beds at the Hyatt Centric on Michigan Avenue would cost $531 but also net me an additional 18,000 Rapid Rewards points. However, I would likely book this directly with Hyatt to earn World of Hyatt points and progress toward elite status... but 18,000 Rapid Rewards points is still quite attractive.

As I prepared to return to D.C. after the holidays, my mother mentioned that hailing an Uber on New Year's Eve would likely be much more challenging than on December 30th. This prompted me to book a flight back to Washington on the 30th, departing at 8:35 a.m.

If you've noticed a pattern, it's that I prefer taking the first nonstop flight of the day. Mornings tend to have fewer scheduling issues compared to later in the day when multiple flights have already taken place.

Total trip cost

When I calculated the points for all three trips—returning home for Thanksgiving, a weekend getaway to Chicago, and then back home for Christmas—the total for flights for my parents and me amounted to just 51,088 Rapid Rewards points. That's quite impressive when you think about it.

After receiving a 100,000-point bonus, I still have nearly 49,000 points left. I could use them to cover a hotel in Chicago, but I've decided to save them for future flights that will offer greater value. Specifically, I'm thinking about a long-delayed beach vacation in Hawaii, especially since Southwest has been expanding its service and providing affordable fares.

One reason I'm okay with holding onto some Southwest points for now is the airline's flexible change and cancellation policies.

If I find myself unable to take any of these trips—due to various factors like a possible COVID-19 resurgence—I can get my points back and use them for future family visits. Who knows, I might even take my parents with me to Hawaii.

My mother has always dreamed of visiting, and since the 100,000 points I earned pushed me past the threshold for a Companion Pass, I should be able to use points for a special mother-daughter getaway.

Final thoughts

While points and miles aren't my primary focus at TPG—since I usually cover daily news—the chance to creatively redeem Southwest points to reunite with my family for the holidays was an opportunity I couldn't ignore. Beyond just crunching the numbers on point valuations, I thought about the added sentimental value of redeeming points to return home for the holidays.

This trip is always significant, but it feels even more special this year after the time we've spent apart.

I've been eagerly counting down the days until I return to St. Louis for our family tradition of viewing Christmas lights in Candy Cane Lane, strolling through Forest Park, indulging in a marathon of Lifetime holiday movies and "House Hunters," ordering thin-crust pizza, and enjoying dining on The Hill at some of the finest Italian restaurants in the city.

Since I work remotely, I'm fortunate to have the flexibility to spend quality time in a different setting from my apartment. For me, there’s no better way to spend this time than with my mom and dad, especially since I haven’t had this much time with them since my college holiday breaks.

As we age, I find myself appreciating this even more, especially knowing that I can use Southwest points with minimal penalties if I need to adjust or cancel my plans. This flexibility is part of why my family has remained devoted members of the Southwest Rapid Rewards Premier Credit Card for all these years. My father, in particular, steadfastly refuses to fly anywhere that Southwest doesn't serve, and while I may not share that exact stance, I admire him for it.