I am not ready to be seduced by Southwest

Now that I'm finally a short commuter train ride, rather than an inconvenient bus ride, away from a Southwest hub I assumed I'd be flying Southwest a lot more. After all, they offer a variety of nonstop flights around the country, Mexico, and the Caribbean, and when "Wanna Get Away" fares are available Ultimate Rewards points are worth more transferred to Southwest than when redeemed for paid flights on other carriers.

But it turns out I still don't fly Southwest, for excruciatingly simple reasons.

Southwest doesn't participate in — or have their own — decent search engines

ITA Matrix is kind of primitive, and I understand that Google is trying to encourage people to use Google Flights instead. But both search engines are great! You can use ITA Matrix to produce a list of flights that correspond to criteria you specify in advance, and you can use Google Flights to alter your search on-the-fly to dial in the airlines, dates, and airports you want to search. Two great tastes that taste great together.

By forcing you to use their own garbage search engine every time you want to find a Southwest flight, Southwest increases by 50-100% the amount of work necessary to compare all the relevant flight options.

Why do I say the search engine is garbage? Here are a few things you can't do using Southwest's search engine:

  • Specify non-stop flights;
  • Specify flexible dates;
  • Specify specific fare classes.

Each of one these requires you to wait for search results to load, and reload, and reload, and reload, while they can all be specified in advance using ITA Matrix or specified on-the-fly with Google Flights.

Southwest is not a low-cost carrier, it's just inconvenient

The reason I've got Southwest on the brain is that I'm trying to plan a Caribbean getaway for early next year and I keep thinking, "I should check Southwest flights." Then I check Southwest flights and get frustrated that I'm wasting my time.

Here's Southwest's one daily non-stop flight from Baltimore to Montego Bay, Jamaica, over Presidents' Day weekend:

And here are two perfectly good American flights (with a connection):

The question to me isn't whether the Southwest flight is "better" or "worse" than the American flights, it's whether the Southwest flight is going to be better by enough, often enough, to justify jumping through their hoops in addition to the ordinary searches I do for paid tickets and awards on real airlines.

Booking Southwest flights can be worth it, but you've got to commit to shenanigans

I don't want to cast aspersions on the judgment of readers who decide that Southwest is the right airline for them. But if you do decide to make Southwest part of your life, there are two important things to keep in mind.

First, always book tickets out of funds in your Southwest account. Most fixed-value rewards currencies can be used to book Southwest tickets in every fare class except "Wanna Get Away" fares. But since Southwest tickets can be freely redeposited into your account and reused, you can apply the credit from your high-value ticket redemptions to cheap Wanna Get Away fares. That means 20,000 Flexpoints can be redeemed for any $399 Anytime fare and that $399 fare can be used to book 2 $200 Wanna Get Away Fares. This is one of the key benefits of Southwest and if you're not using it you're likely leaving money on the table.

Second, consider chasing a Companion Pass. While plenty of affiliate bloggers will tell you how easy it is to earn with Chase credit card signup bonuses, it's also easy to earn through every other method of travel hacking: shopping portals, reselling, manufactured spend, and of course actually booking paid tickets. By doubling the value of your Rapid Rewards points and doubling the value of the funds in your Southwest account, a companion pass can legitimately bring down the cost of Southwest tickets enough to offset the inconvenience of being seated in a cattle car (not that I'm biased).


My older brother is a Southwest enthusiast. He got into travel hacking for the sole and exclusive purpose of getting a Southwest Companion Pass, and he took full advantage of it for 4 years as he got married and had kids. He was sure to check in 24 hours before each flight to get the lowest boarding number. And now that his last year with a Companion Pass has lapsed he's always complaining about how much flights cost.

And that's basically my point: Southwest isn't a low-cost carrier, and it doesn't have any particular advantage in convenience or comfort. It's a lifestyle, and there are a lot of people who are enthusiastic about that lifestyle.

I just don't think I'm ready to become one of them.