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The “Dark Side” of the Southwest Companion Pass

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Dark Side of the Southwest Companion Pass

The Dark Side of the Southwest Companion Pass

Many believe the Southwest Companion Pass is the best travel deal out there, myself included.  Being able to travel with someone for only the cost of airline taxes and fees is a pretty amazing perk ($5.60 one way domestically).  What is amazing is that you can use it as many times as you want. If you plan properly you can even get it for almost 2 years.  Even with all of those positives there is a Dark Side of the Southwest Companion Pass.

Going to the Dark Side

On a recent baseball stadium trip with my buddy, the same one who inspired the negative Airbnb gift card post, I witnessed him go over to the Dark Side.

He earned a Companion Pass via Marriott Vacation packages right before that was shut down as an option.  For our return flight there was a direct flight on Delta for 10,000 miles per person, which he has a healthy stash of, but he decided to take a later Southwest flight.  The Southwest flight had a connection and it didn’t land in Detroit until late in the evening.  He was willing to make those sacrifices to use his companion pass and save a few thousand miles.

When I had my companion pass I found myself doing similar things as well.  I would end up taking a less convenient route or flying at inopportune times in order to use my companion pass.  And I had to deal with a boarding process that I kind of despise as well.

We do these things in the name of saving miles and points.  Our obsession/addiction is real!  We are willing to inconvenience ourselves in order to use a perk and save 10,000 miles etc. In the end is it worth it?  Is it logical? Miles in points are supposed to make travel more affordable but shouldn’t they make travel more convenient too?


I guess the point of this article is to say that sometimes miles and points, or deal hunting, leads us to make illogical decisions.  I am guilty of doing it, are you as well?  Have you ever sacrificed your time or comfort for savings?  Do you still do it or have you moved on from it?

At this point in my life I am willing to pay a little extra in order to find the most convenient routing etc.  The savings just don’t mean as much to me anymore.  And that means that sometimes I would forgo using the Companion Pass to avoid going to the dark side!

Let me know your thoughts in the comments section.



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Mark Ostermann
Mark Ostermann
Mark Ostermann is a father, husband and miles/points fanatic. He left the corporate world after starting a family in order to be a stay at home dad. Mark is constantly looking at ways to save money and stay within budget while also taking awesome vacations with his family. When he isn't caring for his family or taking a weekend trip, Mark is working towards his goal of visiting every Major League Baseball ballpark.

Responses are not provided or commissioned by the bank advertiser. Responses have not been reviewed, approved or otherwise endorsed by the bank advertiser. It is not the bank advertiser's responsibility to ensure all posts and/or questions are answered.


  1. I think the assumption that miles & points should “make travel more convenient” or as one commenter stated, “Points and Miles should make your life BETTER, not worse” is faulty. No one ever promised ease or convenience. Using points and miles is basically a discount program, giving access to flights and/or cabins that one would not normally pay for.

    As with any discount program, people will go to great lengths to take advantage of the freebies, even to the point of inconveniencing themselves, as has been mentioned. We all make the choice every day whether or not it’s worth it to “pay” more for an easier or more convenient experience.

  2. For some of if us it is all about the money, and for others of us time is our most precious commodity. And we all envy those who have plenty of both!

  3. I prefer to pay for a flight like within Europe than use miles and make a connection where I am sitting in an airport for five hours. I can always make more money but I know I can never make more time.
    Each of us must make a value judgement on what our time and comfort is worth.

  4. My addiction had me get the Companion Pass. Had it for 2 years and never used it….hubby refused to fly SW. Got it again for 2 years and made my friend my companion. We used it twice for Vegas trips. Thinking about booking one last trip with it before it expires at the end of the year….but maybe not. Flights must be convenient and non-stop or it’s not worth it to me. The points game is overwhelming. I have way too many cards to manage. I’ve been playing the game for over 25 yrs.

    • It does get overwhelming from time to time and that is why it is important to chase things that work for you instead of what works for many or most. Sounds like the CP and Southwest are not really a good fit for you.

  5. The southwest pass has definitely been a mixed blessing for me. I’ll probably miss it more than I think I will, but I’m looking forward to thinking less about southwest and planning my travels without thinking I could be using the pass!

  6. My wife and I are finishing our 6th year on Companion Pass. We’ve alternated 3 passes. New year’s day 2016 I was so upset when Southwest was not allowing Marriott travel packages to count toward the pass. A few days later, when Southwest realized this no notice change was a big mistake publicity wise, we were thrilled to get a reprieve. We get 10 to 15 trips a year from the pass and will be in mourning if we can’t renew it next Jan. We both got back way under 5/24 so if one of us gets shut down we have a second option. Yes, there is no denying, we have gone way to the dark side with CP. We even fly to Cancun from Tuscon via Denver so we can use our pass. It’s time to get serious help!

  7. As terrific as the Companion Pass is, another of the best things about Southwest is how easy it is to book a flight with points and then, if the fare gets lower, change the reservation and get the difference in points restored to your account. No muss, no fuss, and no deadline or other restrictions on using the returned points, unlike returned cash.

  8. I view domestic travel in the US as a bus service. It takes me from where I am to where I want to go. No flights are more than a few hours. Southwest is perfectly adequate for this.

    When traveling overseas, I’ll spend the points needed to book business on a foreign carrier. This is when travel is luxurious and enjoyable.

    Each has their place.

    • I agree with most of this but there are direct flights vs connections, long layovers etc. There is a big difference there in my opinion.

  9. Psssh, I sacrifice “comfort” all the time for deals. And probably drive our accounting department nuts. I’ve stayed at cheap Wyndham and Choice properties when they are running promos for single nights for 7-night trips, all in the name of points. But when it both saves the company a few bucks and earns me some rewards, who can complain?

    With flights, I’ve gotten a little more choosy. I used to factor in primarily price, either cash or award. Now layovers, total travel time, class of service, etc. all factor into the equation a bit more.

  10. The real “dark side” of getting the companion pass is staying under 5/24 so you can get the Southwest personal and business cards. I keep passing on other opportunities this year for a chance at the companion pass at the beginning of next year. I travel about 3-4 times per year on Southwest so I value the companion pass over 2 years at about 150,000 miles or approximately $2000.

    • Good point Barry – Chase knows what they are doing. Making you pick their cards first and hold on to them longer since they are harder to get.

    • Yes! We had to give away a companion ticket from a Delta Amex because we simply couldn’t use it in time with using the Southwest pass.

    • Lol I feel you there David. I hold onto my UR points like they are going to appreciate in value for some reason 🙂

  11. Mark, I get what you mean. However, labeling it as the “dark side” is a bit of an exaggeration. It’s still a free flight.

    But this phenomenon is not exclusive to the miles and points game. It’s everywhere. People make illogical decisions when it comes to trying to get a deal. For instance, if someone were to offer you $3 to stand in line for an hour, would you take it? Would anyone? I don’t think so. But, if there’s a line for free In n Out burgers, that line would be over an hour long, easy.

    People behave irrationally when it comes to free things.

    • The Dark Side was more a play off of Star Wars more then anything. Agree 100% on free stuff…look at that build a bear deal where people waited 5-6 hours. Insane!

  12. I’ve found myself switching properties in the middle of a business trip and staying in many dumpy Holiday Inns with superior options nearby just to meet Accelerate offers over the last couple of years. My wife would tell me I’m nuts. I prefer to think of it as taking advantage of opportunities. Good article. Sometimes the thrill of the chase just isn’t worth it.

    • I wrote an article debating a mattress run for the last accelerate promo so I am right there with you :). When you sit back and reflect sometimes you just have to laugh at the stuff we do.

  13. Great question to ask for which you will get many comments, but no answer. There is no right answer. Some people drive 5 miles to save a dollar. It’s not worth it if you factor in gas, wear and tear (on car and body), etc. It’s definitely not worth it if you value your time at all. But some people do it because of a personality trait that requires them to get “a deal, the best deal” no matter what. I’m probably like that in my constant search to get a deal. My wife reels me in; partially from her refusing to do some of the crazy stuff I propose, and partially from me being too embarrassed to ask her to do what I’m considering. We find a happy median when I use my points and miles on 5 star resorts and business class international flights. And we always fly non-stop when available regardless of the fact that we have the companion pass. Points and Miles should make your life BETTER, not worse; and choosing a connecting flight is definitely worse than non-stop. Meanwhile, I have done a few “Mileage Runs” and “Hotel Stays” on my own, but I rationalize it by saying that such points, miles, or elite status will make my life BETTER in the long run. Still not sure of the outcome of that.

    • Thanks for the comment Larry and I agree 100% that there is no right answer but the conversation is fun!

      That is what makes a great partnership…counter balance so I am glad that you found it. The chase for status is a fun discussion topic to. I wonder if people enjoy the chase of the hunt as much as they do using it because it becomes a never ending cycle once you get on the treadmill :).


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