Southwest Airlines Tips and Advice!

Southwest Airlines is my favorite domestic airline. I love that they are the only remaining airline that doesn’t charge for bags. I love that they fly out of the three airports nearest to us. I love that they offer direct flights to Orlando from these airports. And I love that they’ve expanded their reach to the Caribbean and Central America. That’s a lot of love. Coincidence that their stock ticker is LUV? I think not!

But how can we make sure that we’re getting the most out of our Rapid Rewards or hard earned dollars when booking flights on Southwest? Here are a couple of tips to keep in mind.


Whenever searching for flights for more than one person, always start your search for one person only. That’s because the prices that Southwest charges fluctuate considerably. They may only have one seat left at a discounted rate (remember that the points they require are directly related to the cash price), but when you search for two or more, they will only show you the higher price (cash or points). Searching for one person will allow you to scoop up the last discounted seat and then you can book the second person at the higher price instead of both travelers.


The big news at Southwest these days is all the new flights to the tropics. They now fly to Costa Rica, Belize, Puerto Rico, Bahamas, Aruba, Dominican Republic, Mexico, and Jamaica. That’s pretty awesome if you ask me. But… keep in mind that using your coveted Rapid Rewards to these destinations may or may not make sense, depending on the cost of the flight.

Why, you ask? In one word, taxes… For example, take a flight to Nassau, Bahamas. A roundtrip flight from Boston to Nassau departing December 20, returning December 24 costs $321 on Delta if you were to pay cash. A roundtrip from Boston to Nassau on the same dates on Southwest not only would cost 27,816 Rapid Rewards, but you’d also be charged $108.23 in taxes. If you ask me, the difference between the cost of a cash ticket and award ticket in this case is not worth 27,816 points.

This is not as much of a concern when booking US domestic flights as the taxes are a standard $5.60 per direction (but you still should compare prices). But international flights are another story altogether. Just make sure that you compare the cost of a paid ticket before assuming that an award ticket and the associated taxes will be a better deal. And this applies to all award programs, not just Southwest.


I know that many of you may be pursuing the Companion Pass through signing up for the business and personal versions of the Chase Southwest Rapids Rewards Visa. I had recommended waiting until October to apply for the current 50,000 Rapid Rewards cards to ensure that you receive your points in January if the Companion Pass was your goal, but I’ve since realized that it’s possible to apply now and have your Rewards deposited in January. As a reminder, the reason why we’d like the rewards deposited in January is so we’re granted the Companion Pass for the remainder of 2016 and all of 2017.

For example, say that you applied for both the Southwest personal and business visas on September 15. That means that you’ll need to meet the spending on your cards somewhere around December 13 (90 days from date of application). But the way that Chase schedules when your billing month closes means that your month will close somewhere around the 5th of every month. Therefore, if your November month closes on December 5, you have 8 days (the time from when the statement closes to when you need to meet your spending requirement) to spend $2,000 on each card so that it hits your Southwest account in January. To put it another way, anything you spend after December 5th won’t hit your account until your December statement closes on January 5th but you’ll need to meet your spending by the 13th in order to receive the sign up bonus. Once your statement closes on January 5, the Rapid Rewards will be in your account a few days later.

I am now the proud owner of a new Southwest Plus personal visa ($69 annual fee), but am waiting on the status of my business application. Given the hassle that many have recently reported when trying to expedite an approval by calling Chase, I’m going to take my own advice and “let it ride.” I will need to employ my favorite manufactured spending technique to meet the spending in the short period in December if I am ultimately approved for the business card. If I’m not, I can meet the spending on the personal card anytime.

In short, there are many ways to leverage the benefits of the Southwest Airlines Rapid Rewards frequent flyer program. Keep these tips in mind to stretch your points and dollars further on future Southwest trips!

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