4 Steps We Took to Save $700+ on Flights to Cancun

This week, after planning out our travel itinerary for all of 2017, it was time to turn to booking and making those vacations we’d planned out in a document actually come to life!

As I discussed in that last post, one of our strategies for elongating our vacations is to book over holiday weekends; unfortunately for cash-based rewards systems (in which the amount of points needed for an award is tied to the cash price of a ticket) holiday weekend are usually more expensive redemptions.

So, sometimes we have to get a little creative. We ended up booking 2 nonstop, round-trip flights from Austin to Cancun over President’s Day weekend on Southwest. The retail price of this trip was $1,012 at time of booking. But we managed to book those same tickets and only spent $276 — just about a quarter of the price.

How’d we do it?

Well, this one took a few steps. At time of booking, the hubby had around 17k Southwest points in his account leftover from work travel this year. I had around 9k in my account. And perhaps most importantly, the hubby had just received 2 $100 “Luv Vouchers” from Southwest for a severely delayed flight experience a few weeks earlier.

Step 1: I booked the most expensive single leg using the hubby’s points stash

This was fairly straightforward. The most expensive leg of this trip was the return flight to Austin at 13,912 Rapid Rewards points. So I booked that with the hubby’s surplus of points, but I booked it in my name – not his. (Reason for that coming later.)

The important thing about this step is the ORDER that I did this. Knowing that I’d be using points for my flights, I needed to book my flights BEFORE I booked the hubby’s paid flights. Because Southwest ties their awards to the cash value of the ticket, and the ticket price is tied to the remaining availability on the flight, I may have risked increasing the points-price of the ticket had I booked the hubby’s paid ticket first.

And, indeed, after booking both his and my ticket, the points price of that return leg has now risen to 17,708 points. So knowing the right order to book in saved me nearly 4k points.

Step 2: I transferred the hubby’s Chase points to my Chase account

With step one complete, my return flight was booked, so I now needed to book my departing flight. Unfortunately, I didn’t have enough Southwest points to book the 13,912 point award flight with the points left in my points stash. (And Southwest doesn’t offer a free points transfer for spouses; you *can* transfer points to other people, but they charge you a hefty fee to do so.)

However, we did still have some Chase Sapphire Reserve points left, and Chase points transfer at a 1:1 rate to Southwest Rapid Rewards. Unfortunately, that card is also in the hubby’s name, and Chase only lets you transfer points to accounts affiliated with the user OR authorized users of the account. Since it costs an extra $75 to become an authorized user, and doesn’t garner you any extra benefits, I wasn’t one.

But, there’s a workaround. Since I also have a card with Chase Ultimate Reward benefits, the hubby was able to do an immediate transfer of points to my Chase account. And then, of course, I could transfer those points to my own Southwest account.

Sunset in Cancun by Flickr user Jose Luis Cruz under a Creative Commons license.

Step 3: I transferred Chase points to Southwest to book my departing leg

So, with an extra 4,000 points recently transferred over to my Chase account, I was able to transfer those at a 1:1 rate to my Southwest account.

Combined with the points I already had in my Southwest account from recent work travel, that was enough to cover the cost of an award flight on the way to Cancun, at 13,912 points. And voila, suddenly I’m going to Cancun, baby.

Step 4: I booked the hubby’s travel with cash + travel vouchers

Now, with my travel secure, I went back to the hubby’s account.  The hubby had recently received two $100 Southwest Luv Vouchers, as an apology for a very bad flight experience on a work trip where he was about 6 hours delayed. So our goal was going to be to use those vouchers on his flights for two key reasons:

  1. Southwest Luv Vouchers expire, so it’s use ’em or lose em.
  2. Southwest Luv Vouchers can ONLY be used for tickets in the name of the passenger to which the voucher was issued.

That second reason is why we used points for my ticket, but cash for the hubby’s, even though moving the points around was a little more labor-intensive. Applying the Luv vouchers, that took the price of the hubby’s RT tickets down to $261.

So there you have it. For longtime readers of the blog, though, you may be asking “but why didn’t you just use your Southwest Companion Pass for the second ticket?” Well, the reason is that our pass is expiring at the end of this year. We’re going to work towards earning it again, but it’s not certain that we’ll have the 2017-2018 pass in time for this trip.

If we DO earn the pass, though, that’s yet another reason that I bought MY fare on points — that would allow me to keep my mostly free fares and still let us CANCEL the hubby’s cash ticket and rebook it for free with the companion pass. Meaning our ending out-of-pocket costs for these flights could end up being even lower, like around the $100 mark for just taxes and fees only!

In the end, all these steps did take me at least a solid hour to complete, and of course, I had to know about all these points and miles rules as well. But if an hour of work can save me $700? Yeah, I’m into that! Here we come, Cancun!

Header photo courtesy of Oasis Resorts in Cancun.


Author: Mrs. Millennial

I'm Whitney, writer of Mrs. Millennial. While I've got an advanced degree and a job in the tech industry, I'm usually happiest in my kitchen, garden, and home, or else on a crazy travel adventure. I hope you enjoy my recipes, home improvement tips, travel stories, musings, and more. You can also see what I'm up to in my professional life at whitneymagnuson.com Need to reach me? Shoot an email to whitney (dot) magnuson (at) gmail (dot) com.

5 thoughts on “4 Steps We Took to Save $700+ on Flights to Cancun”

  1. I really want to invest in a credit card to start racking up travel points when I fly places! I’m fairly new to the whole credit card game (I’m 19) what card do you recommend? Right now I have a chase debit card and a Capitol One credit card.


    1. Hi Alesia! The most important thing, if you’re just starting out in the credit card game, is understanding how important it is to pay off your balances every month. Don’t open ANY credit cards, if you struggle to meet the spend requirements! That being said, if you’ve got significantly more dough than I did as a 19-year-old, I tend to think the best card on the market right now is the Chase Sapphire Reserve: https://unintendeddomesticity.wordpress.com/2016/08/23/introducing-the-chase-sapphire-reserve-card/

      Just make sure you’re being careful with credit as you start out in this hobby!


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