Daydreaming Weekend Trips with Southwest

Ever found yourself bidding on auction stuff just for the heck of it? Or at least getting close to bidding? There’s that thrill that maybe, just maybe you got a deal and get to play with that new toy. I think I found the equivalent in flight award booking last night.

About this time last year, I asked Mrs. Points if she’d like to do some winter weekend trips after the holidays. She gave me a short list and we managed to tick a few off (Winnipeg, Des Moines, DC). It was fun. Last night, the same thought crossed my mind but my tools this year are a bit different. Before going on, let me tell you how most of our award bookings go. I initiate the conversation with my wife and try to get my arms around timing and destination(s), then hunt for availability, obsess over whether it’s a good use of miles, verify friends/family we may visit will actually be there, try to book the award, discover availability shifted some, tweak it, get something acceptable, improve it, and hopefully fly it…more or less in that order. Tedious! If you like puzzles, it can be fun. Sometimes I don’t really want to do a puzzle. Instead, I’m just looking for a quick hit. Something where I can daydream without obsessing about the details and even book the award and hope it works out but cancel it if it doesn’t.

Just in case you weren’t aware, let me give you a couple of details about our situation that makes this all so great with Southwest. We have around 90k Southwest points and can easily transfer more from Chase Ultimate Rewards if needed. We also have at least 72 Airtran/Southwest credits which equates to 9 one-way Southwest trips. Southwest awards are freely cancelled so there’s no harm in booking the trip, then rebooking as the price drops or cancelling if you decide not to go. Finally, I also have the Southwest companion pass so I can bring my wife along for $5-$10 round-trip (taxes) on any trip I book. We have little vacation time but can easily travel and are flexible. It helps too that we have lots of hotel points and friends and family in many places.

Last night I stumbled onto a slightly different approach which really had me looking at new destinations quickly. Let’s take a look at what I was doing and what made it so much fun!

First, set aside your list of where you want to go and open a browser to the Southwest Airlines Interactive Route Map.  Choose the “Nonstop only” checkbox in the lower right and pick your home airport, as shown here:Southwest's New Orleans Non Stops

You may want to make a note of the nonstops you have to work with. If you’re just doing a weekend trip, a non-stop saves valuable time and they’re often cheaper than a connection. It will also be useful as these are your connection points onward to the many other Southwest destinations. Before continuing, ask yourself why you haven’t been to any of these locations? For me, I just noticed that Key West showed up! And it’s been a very long time since I visited Miami (fly into Fort Lauderdale).

Next, uncheck the “Nonstop Only” checkbox. Look for destinations that are served by Southwest or both Southwest and Airtran. It’s a much bigger list but make a few notes about locations that look interesting (my examples, Austin, Portland, Boston) and which perhaps you never thought much about before. Remember that you’re just generating ideas here so be open-minded.

What I looked at for the first time last night was the Special Offers section in the upper left of the site so click that next.

Southwest Special Offers Search

Switch it to a points search, you’ll likely want to lower the bar a bit (since 15k+ one-way tickets aren’t really bargains on Southwest usually), and choose your originating airport, as shown above. A set of “Air Specials” will hopefully be returned. Read the terms, especially the dates. Be aware that they often exclude Sundays and occasionally Friday travel. That’s ok. We’re mostly looking for cities we identified earlier that are of interest and on sale, even if the sale is only on one side of the trip (e.g. cheap outbound, normal return).

Sale Fares

I see some excellent opportunities here… Austin at 9,660 isn’t fantastic but it is on my short list. Fort Lauderdale looks great too and may even be non-stop. Milwaukee, Newark, Ontario/LA, and Oakland all look promising too. Again, ask why you haven’t visited some of the least expensive places. St. Louis is on my list at only 7,620 one-way. Perhaps a quick check of your favorite sports team’s schedule turns up a great opportunity to see a game there or eat the world’s best BLT (can’t believe I finished it with a full malt this past summer).

This might be a good time to pause for a moment before going to the next step and put together a quick calendar of what weekends you can head out of town before actually looking at schedules.

Now, start searching. It’s been a while since we visited New York and, while Newark isn’t our preferred airport, the fare looks great. Fill in your dates (mine are almost always Friday/Sunday) but don’t worry too much about which weekend. From the search results, click the “Try our Low Fare Calendar” link.

Southwest Calendar

Use the calendar to browse weekends that work for your schedule and on the price front. Pay attention to the flights that come back. We’re usually looking for a 5pm+ departure on Friday and a 3pm+ departure on Sunday so as to minimize time off work and maximize time on our trip. A few areas are served by Southwest from more than one airport (e.g. Newark and Laguardia) so you may be able to mix/match

Remember that award tickets are free to cancel. Book it if it looks good and you can spare the points to hold the ticket.

Also remember that Southwest Standard awards using Southwest/Airtran credits can be used too, availability permitting. You can convert points to credits at a rate of 1200:1 (thus 19,200 = 16 credits) and 16 credits creates two one-way “standard” awards. The problem here is that if you don’t have a standard award, you can’t search availability in advance. I’ve had luck calling Southwest and asking them to check availability but I know one friend recently was told they wouldn’t search for him without the credits in his account. It’s worth a try. One nice trick is that if all your standard awards are booked, you can use the Change Ticket function to test availability without actually committing the change. Remember though that credits expire after a year (unless you know the transfer tricks to extend them) and cannot be converted back into points. It’s helpful to have a standard award or two on hand just so you can check availability and, when the points price is over 9600, it’s obvious that you should use the standard award.

Periodically check if the price drops, especially when Southwest announces sales. I’ve caught a lot of price drops making Southwest flights bargains, even without the companion pass.


This got longer than I expected, too common for me, so let me see if I can summarize it. Southwest makes it easy to find sale fares and view them on a calendar. You can also set aside obsessing over value because Wanna Get Away fares are always worth $.01666 to $.018 per point so there’s no question of the value you’re getting. Further, because you can always cancel, there’s no harm in booking first and asking for permission later. Combine this with the companion pass and you can often get a weekend round-trip for 15k points or less for two people which is absolutely amazing.

never thought I’d be such a Southwest guy but then again, I started this whole hobby not to fly up front (though that’s fun) but to get maximum value out of travel dollars and, on the domestic front, virtually nothing comes close.


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