Celebrate 10 Cranky Years with an Insane Day of Flying on Southwest

Cranky 10, Southwest

On August 15, 2006, I published “Welcome From the Cranky Flier,” my very first post. Here we are, 10 years and nearly 3,000 posts later and I continue to chug along, writing and putting together painfully awful graphics. Over the next few weeks, I’m going to put up some Wednesday posts focusing on the anniversary. Today, I’m talking about how I’m going to celebrate.

I wasn’t actually going to celebrate this milestone in any way in particular, but then something came along to change that. On August 9, I’m going to fly 8 flights on Southwest between 9 airports, all within California.

Southwest Insanity

Long time readers of the blog know that I’m mileage-agnostic, and I really have no interest in mileage runs. So why the heck am I going to do something stupid like this? It’s simple math.

Southwest put a targeted offer out to some Californians so it could try to boost spending. The idea is simple. Fly 10 one way flights before October 31 and you get a companion pass from then through the end of 2017. For those who aren’t familiar, the Southwest companion pass is a magical thing. Anytime I fly, I can have my companion fly with me for free (well, plus a few bucks in taxes).

I already had a roundtrip from Long Beach to Oakland last weekend (trip report coming), so that leaves only 8 flights to go. I thought about just running back and forth on $39 fares between Oakland and Long Beach a few times, but that wasn’t really going to be all that exciting. Instead, my crack team at Cranky Concierge got to work.

After searching for awhile (on a rare slow day here at Cranky Concierge), David found the golden itinerary on August 9: eight flights and I never touch the same airport twice.

Southwest 1061 Lv Long Beach 7a Arr Oakland 820a
Southwest 2577 Lv Oakland 1045a Arr Ontario 12p
Southwest 2578 Lv Ontario 1230p Arr Sacramento 145p
Southwest 2262 Lv Sacramento 205p Arr Orange County 330p
Southwest 2370 Lv Orange County 430p Arr San Jose 540p
Southwest 3136 Lv San Jose 650p Arr Burbank 750p
Southwest 3188 Lv Burbank 815p Arr San Francisco 935p
Southwest 2550 Lv San Francisco 955p Arr Los Angeles 1115p

This will qualify me for the companion pass for a mere $505.03. It won’t take too many free flights for my wife to pay this thing off handily. This is going to be fun, even though the chance that I make it on to all 8 flights is probably slim.

This plan is fraught with peril. The morning starts out just fine, and I’m pretty sure that airplane from Oakland to Ontario turns into the flight to Sacramento. So we’re good there. But only 20 minutes in Sacramento? Could be tough. The 25 minutes in Burbank and then 20 minutes in San Francisco don’t leave much room for error. So I decided to reach out to Southwest.

I didn’t ask for any kind of fare assistance. No, not at all. What I wanted was to see if they could put a little asterisk next to each flight so that the ops guys could make these priority flights for running on time that day. While I don’t have a guarantee that this will happen, I know that people over there really liked this idea. I’m going to give it a shot, though if the weather is bad thanks to some freak summer rain, I reserve the right to back out if the deck appears stacked against success.

With that caveat, let’s do this. If you’d like to hop onboard a flight or two, that’ll be fun (do it in the morning). My guess is I’ll be doing this alone, so the plan is to just log on and work all day long. And it’ll be a VERY long day. By the time I get back home, I could have already been in Europe or Asia with hours to spare. Yes, it’s completely nuts, but it’ll be fun. In the meantime, let’s play a game.

What's the chance Southwest's operation holds up and I'm able to make all 8 flights?

View Results

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They say the 10th anniversary is supposed to traditionally be tin or aluminum. It seems appropriate that I’ll be riding on a lot of aluminum to celebrate 10 Cranky Years. I’m also working on another fun thing. I’m not sure I’ll be able to pull it off, but if I do, it’ll be magnifico.

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59 comments on “Celebrate 10 Cranky Years with an Insane Day of Flying on Southwest

  1. I wonder if your Cranky Concierge staff have taken the time to analyze the On-time report for these flights; including if they pushed early from the gate? What would your back up plan be if you missed say the third flight? Can you change the itinerary and drop one of the segments and actually touch an airport twice?

    My vote is 50% at this time.

    1. TC99 – We have all thoroughly reviewed this and it’s early afternoon where things have the best potential of going wrong.

      The morning is easy. Long layover in Oakland, then the same plane Oakland-Ontario-Sacramento. But after that, airplanes start coming in from the east and there are some tight connections. Fortunately, SFO and LAX are the end of the day so that bodes well for on time performance.

      If things go wrong in the LA area, I can just walk away, take the credits, and try to finish it another day. If something goes wrong up north, then I’ll have them get me back to the LA area and save the rest of the credit for later. Only way I’d really get stranded is if that last flight from SFO cancels.

  2. I’m doing a similar thing this week, testing some of the best first class products out there. While I’m going for the super deluxe aspects of travel, your plans sound awesome. You also have a benefit… if something goes wrong? “Just buy a ticket on Southwest, they fly everywhere in CA”. Have fun!

      1. They don’t fly to Monterey either. If they did, I’d quit being a United Platinum guy quickly.


  3. Brett, BRILLIANT idea and good luck. Pack a lunch — or just gonna’ collect peanuts? Take care

  4. This May I decided to burn some UA vouchers in an attempted STL-DEN-SLC-SFO-PDX-ORD-STL routing over approximately 26 hours. I had never been to Utah or Oregon so why not?

    The fun began in STL, where UA had rebooked my STL-DEN-SLC portion through ORD instead of DEN. No biggie, I got to SLC 20 minutes earlier as I had a lengthy layover in DEN, but my window seat DEN-SLC turned into an aisle seat ORD-SLC albeit with an upgrade to Economy Plus. My row mate at the window seat kept the shade down the whole time so there went my scenic views.

    SLC-SFO went without a hitch. Arrived at gate 82, SFO-PDX was from gate 64 so I trekked over there and waited. Gate change to guess where? Gate 82. Same plane I came in on. We boarded the aircraft and the Captain came on with an announcement that maintenance was sniffing around the landing gear. A few minutes later the announcement was made that they needed to change two tires and we could deplane with a minimum 90 minute delay.

    Now I would miss my PDX-ORD flight. So I re-booked SFO-ORD-STL. Got a 757-300 (new type!) but with a dreaded middle seat on a red-eye. Made it to ORD just fine.

    New problem. The ticket agent in SFO did not re-check me in for the ORD-STL section and of course the flight was full. I managed to get on but again, lost my window seat.

    Now UA isn’t WN but you have a couple of tight connections there so I wish you all the best Brett and am really looking forward to that trip report.

    1. Jeremy – I know, I really wanted to do this on a Saturday but Southwest just doesn’t operate any of those late flights on a Saturday night so it wasn’t possible to do it.

  5. Fun! Reminds me of Monday nights when WN was celebrating it’s 25th anniversary. Any flight segment was $25 between certain hours, and WN usually was offering double flight credits to boot. It was fun to see how far we could go and return in the same evening. Another fun thing to do (although it took some planning) was for our airplane geek gang to have a Monday evening dork fest somewhere in the WN system ,granted it was much smaller then but talk about bang for the buck! Also it was the days of $2 Heinekens on board, and back then I had a small arsenal of drink coupons!

  6. Samantha He’s going for 8 flights in one day on SW all within CA never touching the same airport Can he make it??????
    Hahhahahahhahahaha Companion pass awaits!!!!!

  7. What a cool idea, Brett! I’m a longtime Cranky reader (probably 9 of your 10 years) and a noted Southwest homer, but given their recent operations and the experience on my recent trips on WN, I think you are right to question whether this can happen. But regardless, it will be fun to try. Good luck and congrats on 10 great years.

  8. Hey Cranky, what a nutty (SWA peanuts) but fantastic way to celebrate your 10th Anniversary! Congrats and best of luck on connect success. Your nutty ways reflect exactly what Southwest Airlines is all about! Wish I could join you,

    All Day Ray, Flight Training Instructor Southwest Airlines (Retired)

  9. I tried doing something like this twice and never made it. Attempted AUS-HOU 4x back and forth and only made the first leg as the second leg HOU back to AUS canceled which meant leg three AUS-HOU was also canceled. And again LAX-SEA 2x another back anf forth. Never made it out of LAX since the flight was so delayed I could have never made the other three flights. At least back then all the fares were refundable.

    Good luck and I can’t wait to hear how it goes.

  10. I, too, look forward to your follow-up report. Do you think SWA will have really fixed their computer problems by then? On a good day in California (no fog or extreme heat or strong winds or even clouds), you should be OK. SFO can be tricky. You are lucky MRY doesn’t figure in your travel plans. Best wishes.

      1. If it comes off as planned/envisioned, SWA ought to use your crazy efforts in a promotional. I’ll be watching/waiting. Good luck.


  11. so far as of 11 central time the results of the survey look like the bell distribution. how ’bout you put a survey of the ‘chance your rear end holds up through all 8 flights?’ I hear sw airlines’ seats are very thin & unconfortable.

    outside of that i wish i could go for the ride. i’m an airline dork, though probably not at your level or some of your readers. btw, when are you planning to indoctrinate your kids so they become airline “dorks”?

    hope you enjoy the rides.


  12. The real kicker is where the planes are coming from. Good luck — you’ll likely need it. Don’t forget good running shoes. . .

  13. At least you were smart enough not to schedule a tight connection through LAX, you can spend 25 minutes just taxiing on to your gate.

    You know what this is, a rare opportunity for you to review airports! Like come back with observations on which of all these major California port ‘o’ calls stands out (personally, I love San Jose. Not too big, not too small, just right. Nice and airy, and good shops and restaurants)

  14. Lot’s of luck. I would never bet against you in this type of endeavor.

    I’ll bet that probably at least half of your loyal posters have done something like this once in their travel lives.

    My joy was with Mohawk in the 60s. Mohawk had that wonderful “Weekends Unlimited” – “Fly all you want – $25” fare sale. (I liked their marketing–“You may think we’re off our rocker (as our treasurer does) but it’s true, you CAN….”

    A weekend, all day Saturday up to 6 pm Sunday, with reservations having to be made Wed/Thurs/Fri preceding your departure. (If I recall correctly, you could add Monday for a total fare of $45, but how could I get my boss to let me take a day off for this!)

    No internet to help you, so you were at the mercy of the wonderful columnar timetable and the Mohawk res clerk–who probably quit after one weekend of dealing with us future Cranky posters. Off from DCA early Saturday, one F27 and noisy BAC111 after another, across New York state, up and down and back and forth how many times, and eventually back to DCA.

    Wayne Parrish–eat your heart out!

  15. I used to fly WN all over Texas. For some reason this reminds of the day back in the ’90s where I ended up on four planes with 4 different paint jobs in a single day. Standard, Morris Air (which they had just purchased), Shamu and Lone Star One.

  16. I don’t fly WN much, and if I do, only single segment trips. So this question may be stupid, but I will ask it anyway: are these eight individual tickets, or one ticket with eight segments? I should probably just go to WN’s website and see it laugh/barf at me when trying to book it…

    1. Oliver – Well, Southwest’s systems are pretty awful, so this actually required six tickets. I was able to book two of them as roundtrip because the layover time was too short for the Southwest system to allow on the rest. So it’s a whole mess of one ways in there.

  17. So what considerations did you give to congestion at airports or historic performance of individual flights when choosing your connection time? Or did you just go low cost? I find the long layover early on particularly interesting.

    1. AW – Frankly, this was the only itinerary we could find that allowed me to hit all 9 airports in one day. Long Beach had to be first or last, because it only has Oakland service. In the middle of the day, I’d have to do Oakland into Long Beach and then back to Oakland. So that was the only major constraint. Then it was just trying to fit the pieces together. The good news is that it actually looks fairly solid. Here’s how it looks flight by flight.

      Long Beach – Oakland: Plane spends the night in Long Beach, so this should go well. Also, I have a ton of time in Oakland even if it is delayed.

      Oakland – Ontario: It looks like the airplane stays on the west coast in the morning so hopefully it gets there on time, but there is a little flex because….

      Ontario – Sacramento: This appears to be the same airplane that brings me into Ontario so I have no concerns

      Sacramento – Orange County: This is where I start getting nervous. The airplane goes Pittsburgh-Chicago-Phoenix-Sacramento, so any weather delays in the east could mess this up. I do have an hour in Orange County though, so even a 40 minute delay would be ok.

      Orange County – San Jose: This airplane comes in from Austin and who knows where before that. Weather could delay this one as well, but I have 1h10m in San Jose, so that’s good..

      San Jose – Burbank: I’m not positive, but I think this one may hang around the west coast. But after a long day of flying, it could run late. I can’t afford that.

      Burbank – San Francisco: I think this is the same airplane as the one from San Jose, which is good. SFO doesn’t tend to have much fog later in the evening, so I’m hopeful this won’t be delayed.

      San Francisco – Los Angeles: Frankly, it doesn’t matter if this is delayed as long as it doesn’t cancel. And I bet it will delay. Southwest is dedicating 737-300s to this route right now. These are the ones with the old comfy seats that are supposed to be retired soon. But hey, a delay on this won’t matter.

      So, that’s how we thought about it. We’ll see how it turns out.

  18. Always book only One Way tickets on Southwest. They dont cost any different, and you have the most flexibility on cancling and re-faring.

    Lets say you have a round trip ticket, SFO-LAS. You bought it 2 months ago when there was a sale. But now the day you are supposed to fly to LAS you find out you have to be in LA for work. You have to cancel you entire trip, and rebook, a probably way more expensive LAS-SFO ticket. But with one ways, you just kill the SFO-LAS segment, buy a LAX-LAS ticket and you are still good to get home to SFO.

    Also, Cranky, did you buy early bird check in for any of these?

    1. Jeremy – No EarlyBird at all on this one. For half of them, it won’t matter. Boarding will have begun by the time I get there anyway. And honestly, I’m not expecting these flights to be all that full on a random Tuesday. I’m just going to check in 24 hours in advance and take what I get.

    1. Micah – Funny you say that. I’ve been playing around with this new app Busker since a friend of mine is involved with it. I was thinking I might try to do it with that one (assuming the Android version launches before I go, as expected). The only problem? No friggin’ power outlets on Southwest. I may need multiple devices.

  19. Sorry for ignorance but what does WN stand for?
    And I believe this is gonna work. If for no other reason than SW is going to be watching this closely and trying their best to avoid bad press. SW might have someextra planes left along that route to roll out that would not otherwise have been there I say 90% hahahhahahaha

      1. It would be interesting to see a post about irregular airline codes that do not match up with their names like HP-America West, WN-Southwest, G4-Allegiant, etc. and how they came about getting their designations.

        1. TC99 – For the most part, the stories are the same. “What we wanted wasn’t available so we just found the closest thing we could.” Generally two letter codes were considered more prestigious, but at some point, airlines just took what they could get. For America West, the joke was that it meant Happy People or Happy Passengers. I’m guessing that was just the legend made up after the code was adopted. I don’t really know any good two letter code stories, but I’m sure there are some. Anyone?

          1. NK for Spirit stands for Ned’s kids. Ned Homfeld was the founder and the story is that his employees were like his kids.

  20. I wonder how you were able to figure out the flights. Just for fun, I tried to build such an itinerary (from NYC) and it’s very hard to find a good set of flights

    1. Bruce – We copied and pasted all the flight schedules between the Bay Area/Sacramento and LA Basin airports. Then it just became a puzzle. We kept getting closer but couldn’t quite get there until David came across one that worked.

  21. Brett,

    This is one cool idea. It’s more than a year ago that my blog passed the 10 year mark and I an sad to say I marked the event with nothing. People on the outside looking in just have no idea of the single-mindedness and dedication it takes to keep things going consistently as you have. Especially since you have built and run a successful business as a “sideline” (ha ha) during this time.

    Keep flying and keep writing for at least another 10. I’ll be following you on FlightAware on the 9th. Best of luck.

  22. My only question is boarding passes. What I don’t like about Southwest is you can only have two boarding passes at one time. Many times, especially with an overnight trip, I have been stuck with B and C since I have 4 flights within 24 hours. How did you get pass that?

    1. Jason S – I think that’s only on a single reservation, right? On separate reservations, I should be able to get all the boarding passes I want, I think. If not, oh well, it’s C for me.

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