Tag Archives: Southwest Airlines

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I Cancelled My Last Minute Trip to Hawaii [Rescheduled for June]

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Reposted on 3/17/20 at 7:30am

Updated 3pm PT on 3/14/20: I was planning on going to Kauai in March but have rescheduled my trip to Kauai for June.  I have cancelled / rescheduled all the reservations below.

Good afternoon everyone, I hope your Friday is going well.  As a sequel to yesterday’s post (I Cancelled My Trip to Ireland), we decided to go to Kauai instead for Laura’s spring break (we went to Kauai 2 years ago for Laura’s spring break as well).  I checked flights from the Bay Area to Hawaii and flights were in the $100-$130 price range each way to all the Hawaiian Islands.  Prices were so cheap that it was a better deal to pay for flights than to book award tickets.

Laura had ~52K Southwest Airlines Points in her account, so we booked 2 roundtrip tickets from Oakland (OAK) to Lihue, Kauai (LIH) using 50,292 SWA points and $22.40 in taxes/fees ($5.60 per person per flight).  About an hour later, I checked the flight prices and saw a price drop.  I immediately rebooked the SWA flight for free and saved 8,174 SWA points.  This morning, I checked the flights again and saw more price drops.  I quickly and easily rebooked those flights using the SWA app.  After the dust settled, our SWA flights now cost a total of 35,087 SWA points (a savings of 15,205 SWA points in ~12 hours).  I kind of feel bad that the prices keep dropping so dramatically (but I will keep checking the flight prices to see if they get any cheaper).

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My Travel Philosophy for Redeeming Miles vs. Paying Cash for Flights (w/ Account Balances as of March 2020)

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Good morning everyone, happy Friday!  I just finished listening to the Miles to Memories podcast (latest episode) and enjoyed listening to them talk about Disney when they redeem miles vs. pay cash for flights.  I don’t have a hard and fast rule that I live by, so I thought it would be fun to share my travel philosophy of when I redeem miles vs. pay cash for flights.  I specifically mention flights because I plan to write a similar article about hotels and didn’t want to make this article too long.  Lastly, when I use the word cash, that could mean paying for the flight with a credit card, or paying with an airline gift card, or using credit card rewards to pay for the flight – basically anything other than booking an award ticket with airline miles.

I also think it is important to share how many credit card reward points I have, since my thinking would be much different if I had 1,000 Chase Ultimate Reward Points vs. 1 million Chase Ultimate Reward Points.  With that said, here are my transferable points balances, as of March 2020, from smallest to largest:

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2 Buy Miles / Points Promos Ending Soon: American Airlines (55%) & Southwest Airlines (40%)

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Good afternoon everyone.  I was working on my Buy Miles & Points Page and found a few offers ending soon.  Always check the math to make sure that buying miles & points makes sense for you.  Do not buy miles & points speculatively unless you have a use in mind.  With that said, here are 2 offers that end this week.  Up first, American Airlines is offering up to a 55% bonus + 10% discount, depending on the number of American Airlines AAdvantage Miles you purchase.  This offer expires on March 6.

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Use American Express Chat to Change Airline Fee Credit Airline Choice (Almost 100% Automated)

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Good morning everyone, I hope your weekend is going well.  Yesterday, I booked an American Airlines flight from New York (LGA) to Dallas (DFW) to Orange County (SNA) for Laura and myself (we plan to check out the Centurion Lounges in LGA and DFW during our trip).  With my American Express Gold Card, I get a $100 airline fee credit to use each year to cover seat assignments, checked bags, in-flight drinks/snacks, etc.  I decided to use my $100 airline fee credit to purchase preferred seats for our American Airlines flights.

Unfortunately, American Express has a weird system that will automatically enroll you in last year’s airline choice if you do not make a change by January 31.  Since I selected Southwest Airlines in 2019 (when buying Southwest Airlines eGift Cards triggered the credits), that was who my airline choice was for 2020.  Thankfully, you can change your airline choice if you do not use any of the credit in the current year.  Instead of calling American Express, I clicked the Chat button in the lower right corner of the screen.

I typed in my comment and the automated system asked me a few questions.  After going through the prompts to change to American Airlines, I thought the Chat box was going to make the change for me, but unfortunately, I had to be connected to human.  After confirming my airline choice, the agent processed my change.  I’m not sure why the Chat box could not do it by itself, but the whole process only took a few minutes.

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4 Buy Miles / Points Promos Ending Soon: JetBlue (40%), Southwest (30%), British Airways (30%) & United (75%)

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Good afternoon everyone.  I was working on my Buy Miles & Points Page and found a few offers ending soon.  Always check the math to make sure that buying miles & points makes sense for you.  Do not buy miles & points speculatively unless you have a use in mind.  With that said, here are 4 offers that end this month.  Up first, JetBlue is offering up to a 40% discount, depending on the number of JetBlue TrueBlue Points you purchase.  This offer expires tomorrow – January 23.

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