The Southwest Companion Pass is [arguably] the best value two credit cards can get you. I mean, anytime you fly, one person gets to fly with you for free! Doesn’t matter if you paid in points or cash, the second person’s flight is free.

This Companion Pass lasts the entire rest of the calendar year, and all of the next calendar year. Potentially two years of free flights for one companion. Plus, you have 110,00 Southwest points which qualify for the free flight.

Personally, we had this thing most of 2011 and all of 2012 and by the time it expired we still had more than 30,000 Southwest points left. Took ~13 flights and still lasted the entire time for us, and then some.

Here’s what you’ll find in this post:

• Getting the companion pass
• Timing your companion pass
• How to Make Your Companion Pass Last Longer
• Finding Southwest Deals
• Caribbean Destinations (and all points hotels)

Getting the Companion Pass

I’ll briefly mention how to get the companion pass. Basically, it’s a Southwest benefit, kind of like a “top tier status”, but instead of lounge access, you get a companion pass. To get it, you need to earn 110,000 Southwest Points within one calendar year. To make things better, points earned through the Southwest credit cards count towards the companion pass.

To makes things sweeter and more convenient, the Southwest credit cards often run 50,000 point bonuses. So if you got both personal and business versions, that’s 100,000 bonus points right there. But after meeting the $6,000 spend requirement (for both cards), you’re really only left with 4,000 needed points to earn the companion pass, which could be done by spending another $4,000 within that year.

Timing is everything.

Getting the 110,000 points knocked out in the beginning of the year will give you a full two years. Got it? Because, again, you get it for the rest of the current calendar year, and all through the entire next year. Getting it early in the year, is best.

Technically, you don’t have to apply for the cards at the beginning of the year, either. After all, it takes time to get approved, get the cards, and get the spend done. But here’s a little trick: Assuming the 50,000 point credit card offer is around, apply for the cards in December of the year before you want the Companion Pass. But instead of spending the full $3,000 to earn your spend requirement, wait to set off the bonus until January. Let all your points post in January.

The important thing is to try to get your points to post in your Southwest card as early as possible within the same calendar year, to enjoy the Companion Pass for up to two years.

Okay, now we have the Companion Pass, then what?

Now you need to understand how long your 110,000 miles will last you. Because, the two of us, we want 20 flights out of our miles, not the advertised “2 roundtrips” for the 50,000 points. How long can we make the free last?

Basically, you have to watch for sales, just like revenue tickets. Because Southwest doesn’t do award availability or pricing like any other airline. To get the “points price” of a flight take the regular paid ticket price and multiply it by 60.

A $100 flight, will be ~6,000 points (60 x 100 = 6,000).

Another way of thinking about it is that with 110,000 Southwest pints, you’ve got $1,833 worth of flights with Southwest (and the second person is free).

The real question is, what would you do with $1,833 worth of flights. Forget that you actually pay with points. Again, the points are worth just 60 times the regular flight price. And therefore, you need to look for sales.

Finding Cheap Southwest Flights

The best way to find cheap Southwest flights on points, is to find cheap Southwest points on cash. The best way to do that is flash sales, Ding, and timing.

Analyzing flight times

Southwest has a function that shows you the lowest price on their low fare calendar, be it points or cash.

This can help you find when prices start going up, typically speaking.

I’m writing and researching this on Aug, 15. When I do a search for flights from today onward with the calendar, you can clearly see prices rise as the date of travel gets closer. The week of, at 27,000+ points, then the next week drops off to 8,000 points. The next week drops again to 6,900 points. But by the 4th week prices had dropped to a low average of 5,470 points.

I also looked at LA to Columbus, Oh. The week of things seem to be 17,000 points, but one day (on the weekend) is 49,000 points. Week 2 a fews dates show 10,000 points, and then finally by week 3 it seems to level off with that as a constant price.

You can do this for all kinds of routes. You may learn a few things, like Southwest prices go up within the month of travel, by a lot at times. Another thing I can’t help but notice on many routes is that weekend prices are higher. Southwest, unlike Delta and United has most of their customer base as leisure travelers (instead of business travel).

Southwest Sales

Click N Save

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https://www.southwest.com/html/email/click_n_save_signup.html

Ding

But the bread and butter of sales is Ding. Choose what airports you’d like to get alerts for (up to 10) and when you see them, click.

https://www.southwest.com/html/ding/what-is-ding.html

Plus, you can find sales periodically on the home page, but these will probably get emailed to you anyways if you signup for the first.

Throw away trick

Chances are if you’re flying to one of these cities, you’ll have plenty of options for flights. But what’s interesting is that some of these sales are for specific city pairs regardless of routing. Like for example, I saw a flight one time that was Little Rock to Dallas on sale, and a flight to Dallas was cheaper than a flight to Houston… even though you could route through Houston. For whatever reason, flying to Dallas via Houston was cheaper than flying to Houston. One could get off the plan and “throw away” the ticket to Dallas (just not fly it). But know the rest of your ticket will be cancelled if you skip a flight (which doesn’t matter if it’s the last segment of a booking).

Here are some hubs (focus cities) you might be able to route through to strategize your throw-away ticket.

• (BWI) Baltimore–Washington International Airport
• (MDW) Chicago Midway International Airport
• (DAL) Dallas Love Field
• (DEN) Denver International Airport
• (ATL) Hartsfield–Jackson Atlanta International Airport
• (STL) Lambert–St. Louis International Airport
• (LAX) Los Angeles International Airport
• (LAX) McCarran International Airport (Las Vegas)
• (BNA) Nashville International Airport
• (OAK) Oakland International Airport
• (MCO) Orlando International Airport
• (PHX) Phoenix Sky Harbor International Airport
• (SAN) San Diego International Airport
• (HOU) William P. Hobby Airport (Houston)

 

Go, Cancel, or Match a Lower Price

There’s no reason to wait on booking a ticket you think you’ll take. Southwest, (sit down for this), is fee free. Southwest has no fees for cancelations or changes. Book, and if you can’t go, cancel.

And they’ll match a better price. Which means you can book a ticket, and if you see a lower price you can rebook it and it will refund you the difference. I’ve done this online a few times and it’s easier than… pretty much every other airline.

We got lucky and hit a string of sales, and before the slight deval, giving us a number of tickets for 3,000 – 4,000 points. They were short flights like CMH – LIT, LIT – HOU, and CLE – LGA, but 3,000 points for two is unbeatable. Especially when you have 110,000 points.

Best Southwest Destinations

Southwest is primarily a domestic airline, and has great coverage of the US, but has a few flights to the Caribbean as well.

• (SJU) San Juan, Puerto Rico
• (AUA) Aruba
• (MBJ) Montego Bay, Jamaica
• (CUN) Cancun, Mexico
• (SJD) Los Cabos, Mexico
• (NAS) Nassau, Bahamas

Coming soon, on November 2, 2014 is:

• (MEX) Mexico City, Mexico
• (PUJ) Punta Cana, Dominican Republic

Direct flights can be super cheap. Pick a city and a Caribbean destination and see where it routes through. I noticed flights to Jamaica sometimes route through Orlando. I looked up Orlando flights, and they are 3,290 points! And for two people, that’s the cheapest flight deal I think I’ve seen. That’s basically 1,645 points per person, per direction… To Jamaica!

The thing you may notice is that even on Southwest flights, you have airport taxes. In the US, that’s typically $5. Your companion still has to pay these taxes. Not a big deal.

But with international flights, they can be as high as $65 (leaving Jamaica). This is because there are at times international taxes, and most countries have higher airport taxes.

Doing what I always do, I made a spreadsheet based on taxes to/from, for direct flights. Destinations are in order of cheapest to most expensive departing taxes and fees.

Airport	Going to	Departing from
SJU	$5.60	$5.60
AUA	$15.60	$55.00
CUN	$29.19	$53.92
MBJ	$49.60	$60.90
SJD	$29.19	$60.84
MEX	$29.19	$61.81
NAS	$5.60	$93.50
PUJ	$36.90	$93.66

This is an unfortunate reality of the Caribbean. Taxes and high fees are unavoidable. The best you can do is use your World Arrival+ to get reimbursed for those fees. But compared to a $10 roundtrip ticket to another coast, you’re looking at $100+ per person with some of these routes.

Then again, SJU is basically a domestic ticket. So there’s one normal option.

As a little bonus, I decided to make a chart of the points hotels at each of the Southwest Caribbean locations:

	Hilton	IHG	Club Carlson	Marriott	SPG	Hyatt
San Juan	40,000 – 50,000	15,000 – 50,000	38,000	25,000 – 40,000	7,000 – 30,000	8,000 – 25,000
Aruba		25,000	50,000	35,000 – 60,000		25,000
Cancun		15,000 – 35,000		35,000 – 50,000	3,000 – 10,000	25,000
Montego Bay	fluctates	35,000				?
Los Cabos	fluctates	20,000 – 35,000		7,500	10,000	20,000
Mexico City	10,000 – 50,000	10,00 – 30,000	15,000 – 28,000	7,500 – 30,000	3,000 – 16,000	15,000
Nassau	40,000
Punta Cana		15,00 – 25,000			2,000 – 12,000

Maybe someone else was curious as well…

 

Domestic

Besides, the Caribbean, Southwest covers the US very well, including most every major city.

I mean, I can’t begin to name all the awesome destinations domestically. Nor could I name all the hotels…

But you should follow the maps I’ve been making, click to show lower categories and get an idea of lower level redemptions for the chains you have points in.

Click Here to see the Complete Maps for each hotel chain (at least the ones done so far).

Either way, most all these programs have a ton of hotels in the US.

Conclusion

This is our second time with the Companion Pass (first time it was in my name, this time in Carrie’s name), and I hope to make the most of it. I really hope to run my account dry of Southwest points and make the most of this 2014/2015 Companion Pass. We’ll get back from Central America mid/late September and then have a month or two to start our burning.

In the end, the Southwest Companion Pass is one of the most generous benefits of any of the credit card perks. If 110,000 points is worth, $1,833, then the points plus the added second person would be a value of $3,666… from two credit cards.

Now you just have to wait for another 50,000 point bonus for both cards. Or… you can wait until next year.