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

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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.

Neil S.

It’s a cool idea and I’m excited to see if it all works.


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!


SW flys everywhere in California except Fresno. We wave to them as they fly over.


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


Roger Cohen

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

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… Read more »

Aug 9, sigh, too bad its a Work Day.
If you get stuck in SFO, give me a call

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… Read more »

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!!!!!


BS : You rock!

Eric in ICT

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.


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)

David SF eastbay

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.


Numbers legend for legs 5-6 and 7-8 is reversed on the picture.


Hey, you left out San Diego :-)


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.


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.


Jim M

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


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)


Have fun – and congratulations.

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… Read more »

Congrats on 10!


This is Amazing. And borderline insane. Thanks for sharing and good luck!


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.


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…


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.

Nick Barnard

So you’re spending the day before checking in to make sure you get A boarding?

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… Read more »
Micah Child

Live Stream or it didn’t happen ;)


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


This sounds awesome! Almost as awesome as flying out to LAX for a day to watch planes…almost. :)


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

Dave Starr
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.
Jason s

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?


Good luck !… Hope you’ll be tweeting live !