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Make the most of your miles! Award booking strategies for Southwest flights.




We’re going to try to dive in to strategies for booking award tickets on various airlines. First up, since we picked up an additional two months of schedule this morning, is Southwest. It might seem like the easiest program to use, but there are a few extra things worth keeping in mind.

Miles or points to use:

Southwest points – there are no partner programs that can be used to directly book award tickets on Southwest flights.

Besides Chase Southwest credit cards and the Southwest shopping portal, Chase Ultimate Rewards points, Diners Club points, Hyatt hotel points, Choice hotel points and Ritz-Carlton hotel points are all viable transfer partners for collecting Southwest points.

When to book:

When you have the points and think you might be traveling. Seriously, book it. You don’t have to think about it, confirm dates, ask for time off or anything else. Just book it.

Failure to think this all the way through and act on it is the biggest mistake I see people make (and have made myself). Cancellations of points bookings are absolutely completely free. No catch. If you don’t bother to cancel and just don’t show up, you get your points back but not your taxes.

I’ll give a couple of my own examples: going to Charlotte for FT4RL2, I’m flying on the day that Spring Break begins here in Texas. There have never been any saver level seats on any carrier, and the 13K points ticket I booked is the best price I’ve seen. Bonnie didn’t think she’d be able to go so I booked only for myself. Completely stupid, I knew the price would go up! Sure enough, I wound up booking for her a month later at 20K points. A second example is a trip I booked today. We would like to go to New England and just explore in the fall, so within an hour of the schedule opening for October I booked one-way tickets to Portland, Maine and home from Manchester, New Hampshire. Will we actually spend Columbus day weekend wandering around New England? I have no idea! But if the fare drops, we get our points back. If we cancel, we get our points and money back.

If you have the points and may need a ticket to anywhere Southwest flies, book a speculative Southwest ticket with points now, and work out the rest of the details later!

Southwest destination map, soon to include Costa Rica and laterBelize City.

Southwest destination map, soon to include Costa Rica and laterBelize City.

Booking difficulties:

For most domestic travel, there aren’t any difficulties. Search, book, keep an eye on your ticket’s price and get a refund if it goes down. However, if you live in a city with infrequent service or just can’t find what you’re looking for there are a few things you should know.

Southwest will not give you a layover of over 4 hours, which also means no overnight layovers on a single one-way. Here are a few examples of ways around that rule:

Getting a better route when the only ones available in a simple search aren’t what you want

This is an example of a problem I’ve run into a few times when flying out of a city like Charlotte which has only a few flights each day. There are few available routings, and none I want.

Routes for this ticket are awful - the last one routes through Chicago and Denver!

Unless I want an early morning departure, routes for this ticket are awful – the last one routes through Chicago and Denver!

Nothing here works for what I want. However, if I check the Southwest route map for nonstop routes leaving Charlotte and then search those routes I find a 10:20 nonstop flight from Charlotte to Houston. I could search separately, but it’s easier to click ‘Add another flight’ at the top of the selection screen and change my search to CLT-HOU with SAT in the third box:

Much better, a midmorning departure that doesn't take me way out of the way!

Much better, a midmorning departure that doesn’t take me way out of the way!

The remainder of the screen shows the HOU-SAT flights. The 4-hour rule was preventing CLT-HOU-SAT from showing up in our first search.

I'm not crazy about the price, but this routing might be worth the additional 4,000 points.

I’m not crazy about the price, but this routing might be worth the additional 4,000 points.

By selecting the 10:20 and 4:40 flights, I have the ticket I want in one booking. I could, of course, also choose any later flight if for some reason I wanted to spend the afternoon in Houston.

Even with a 4+ hour layover, the total travel time here is less than the crazy CLT-MDW-DEN-SAT routing offered in the first search!

Even with a 4+ hour layover, the total travel time here is less than the crazy CLT-MDW-DEN-SAT routing offered in the first search!

Getting around unpublished routes

A much more common occurrence of the same problem, with the same solution, often occurs on travel from the West coast to the Caribbean. While Southwest is slowly improving availability of these routes, many are still impossible in one booking. Here’s a search from Portland, OR – Montego Bay, Jamaica:

You can't get there from here.

You can’t get there from here.

By clicking on Portland and then Montego Bay on Southwest’s route map we see that the possible one-stop routes are via Chicago and Baltimore. This looks like the best combination of flights for our Friday departure in August:

24,892 points and $55.20 one-way is hardly a bargain unless you consider the competition for the same date. And of course you can use a companion pass here.

24,892 points and $55.20 one-way

This is hardly a bargain unless you consider the competition for the same date. In a search for 4 passengers on that date, there are no saver level seats on any of the legacy carriers. With Delta, AA/US or United miles, similar routings are available as well as redeye flights, for 35K – 37,500 plus $49-$52. If we keep searching other nonstop Portland flights and are willing to make an extra stop, we can get the Southwest price down to 20,971 points. And of course you can cut the number of points required with companion pass(es).

PDX-MBJAny of these domestic-and-international tickets must be booked separately, unlike the all-domestic example shown above. Hopefully the new international terminal opening soon at Houston’s Hobby Airport will allow Southwest to improve the schedule of many of their international routes.

Other stuff you should know:

In case you’ve been living under a rock or are completely new to Southwest, you can earn a companion pass by earning 110,000 points within a calendar year. Bonnie and I each have one which allows our boys to travel for no points, just the taxes of $11.20 on a domestic trip or $60-$90 for international. While the easiest path to a companion pass for many people is a pair of credit cards and $10,000 total spending, it’s certainly not the only way. In fact, thanks to a couple of nice reselling opportunities I’ll likely earn a companion pass again this year for 2016, even though I already have one through the end of 2015!

Southwest has excellent phone service if you have a hard time getting awards repriced due to a new lower price. Just don’t try to add your child as a companion on an international itinerary on the day the schedule opens up!

Southwest has announced that the value of points will change for some trips beginning in April. Currently they are worth about 1.5 cents each (or 3 cents if you’re using a companion pass). We don’t have any specific details, but speculation centers around potentially lower point values for international and/or peak travel dates. Here’s what Southwest has told us:

We created Rapid Rewards® because we think you deserve to actually feel rewarded. And, from time to time we must make some updates to our program. Beginning April 17, 2015, the number of Rapid Rewards Points needed to redeem for certain flights will vary based on destination, time, day of travel, demand, fare class, and other factors. However, there are still many flights which will stay at the current redemption rate. And don’t forget that when fares go on sale, so do the points needed for redeeming for a reward flight on those fares.

Southwest has assured us that the most valuable (in my opinion) aspects of their program, completely free cancellations and the companion pass, will remain unchanged. Unfortunately their next schedule extension (through January 4, 2016) will not occur until after the April changes, so fall and winter holiday travel late this year will be at the new rates.

That’s Southwest award flight booking, both the simple and the slightly more complex. Remember, if you have the points go ahead and book tickets for any travel you might take, even if they are just placeholder tickets and you plan to book with another airline or award program later!

– Kenny

{ 9 comments… add one }
  • Kumar February 19, 2015, 6:16 pm

    Useful, as usual. My only complaint against Kenny is the low frequency of articles. Come on, you are certainly one of the best out there. I think you should be writing more compared to those pumping “titans” who are churning out useless articles just to sell.

    • Kenny February 19, 2015, 10:27 pm

      Thanks Kumar, I really appreciate it! Between work, kids stuff, actually traveling (yeah we do that!) and trying to help people out with specific questions, there’s only so much time left! Which is probably just as well since there’s only so much content we could put together without regurgitating the same stuff or pushing plastic. No thanks.

  • Narayan February 27, 2015, 2:04 pm

    Nice article Kenny. Have been just catching up with your blogs.

    My biggest problem is I have been unable to get the Companion pass. Tried once before when I got the personal but Chase did not give me the business card. Have to try again this year, maybe and hope that they give it.

  • bluecat March 1, 2015, 3:52 pm

    Hi Kenny,
    I have to admit that this post is hard for me to follow…in fact, I’ve read and reread it but I don’t get your screen posts and what you are trying to show. If I can make a couple of suggestions: (1) clearly state what you are trying to do and then (2) what the problem is you are running into (e.g., the SWA engine doesnt show more than a 4 hour layover).

    In your example, I think I figured out the one way you are trying to achieve but then this part is a little hard to figure out: “However, if I check the Southwest route map for nonstop routes and then search I find a 10:20 nonstop flight from Charlotte to Houston. So I click ‘Add another flight’ at the top of the selection screen and change my search to CLT-HOU with SAT in the third box:” — I think the point you are making is to “try to get in the neighborhood” and this is the crux of your “trick”. I never actully figured out why you put your endpoint in the RT city field unless this is another trick to save miles(?). (BTW, this sort of “trial and error” approach is ripe for a short movie and great for your next seminar. 🙂 )

    Finally, I would just (3) emphasize/reiterate the “tricks” that you suggest people use in the conclusion.

    Anyway, you know I’m a huge fan so please take this as me trying to add (not detract).

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