The nightmare that was the Southwest section in Midway Airport in Chicago on Thursday, July 24, 2016.

Warning:  LONG post ahead, but I think a worthy read.

My story is not unique, which is why it’s so important to tell.  But what is below represents one of the worst customer service experiences of my life, combined with rudeness and blind indifference – by an airline that is supposed to be the friendliest out there:  Southwest Airlines.

I am definitely NOT nuts about Southwest

I will start off this with a disclaimer:  Southwest suffered a computer outage on July 20, 2016, a day before I was set to travel to Omaha, Nebraska to help a friend move.  Boy, do I wish I had read the papers that morning because I would have changed airlines in a heartbeat.

On Wednesday, July 20, 2016, Southwest suffered “computer outages” that essentially grounded their entire fleet, causing more than 700 flight to be canceled.  And all of those people who were grounded with the Wednesday flights were trying to get on them the day that I was flying – Thursday.  It seemed like a once-in-a-life-time event, but it boggles my mind how an airline what built its reputation on online service could have everything go “poof” at once, like a clumsy IT employee tripped over the extension cord powering their servers.

Where Southwest blew it – repeatedly

When I showed up for my flight unaware of any problems (they text me all the time; couldn’t you warn me before this?), I discovered that, after getting in line (first) to board for my stopover in St. Louis, that the flight was canceled.  That’s right; they made us line up like cattle, raised our hopes, opened up the door to the jetway, THEN announced that the flight was canceled.

Like an Olympic sprinter, I headed straight for a Southwest desk and got on another flight to Chicago Midway, then on to Omaha.  No problem, right?

Where the nightmare began

Since I was literally the last person to board a full flight, as I was boarding the plane with my CARRY ON-SIZED LUGGAGE, the flight attendant at the door told me that I was going to have to check it.  I expressed hesitation because of what was in the bag:

  • Medications for my heart that I HAVE TO TAKE EVERY DAY;
  • All of my clothes
  • Hearing aid batteries
  • My glasses, without which I am blind
  • All electronic device charging cables (needed to communicate with Southwest – keep reading)
  • So, so much more.

What did the flight attendant tell me?

Unless you give us your luggage, you will not be allowed on the flight.

So I hurriedly grabbed what was on top:  my iPad and laptop. When I tried to grab the clear, plastic bag with my life sustaining medications in it, the flight attendant told me that I could NOT bring the bag because it would not fit in the seatback compartment ahead of me.  She was rude as one could be as all I was trying to do is avoid the nightmare that I faced.  As she put a tag on it, I READ HER the number of my flight to Omaha (four-hour layover in Chicago), I told her that I had critical medications in the bag.  She told me that the bag would get to Omaha before I did.  Um, not so much.

Oh, if only that were the case.

The nightmare begins

The flight to Chicago Midway was uneventful, so I had time to wander.  So rather than waiting five hours, I went to a Southwest counter and got on an earlier, 3:05 flight.  I went to the gate, waited, paid $30 AGAIN to get upgraded to priority boarding, was called to stand in line and the Southwest ticket person opened the door to the jetway.  “Things are going to work out fine,” I thought.

Not so much.

First, the Southwest ticket taker who was just staring out the window at the plane announced that we were waiting for another flight attendant to board the plane.  We had two pilots, I assume plenty of fuel to get us there – and by the way, I don’t really give a damn about my glass of water and bag of peanuts.  Just get the damn plane off the ground.  I would have handed out drinks myself.

So we waited in line.  For 30 minutes.  Finally, the staring-out-the-window Southwest employee announced that the flight had been canceled.  And the next flight (5:55pm) was the one that I had given up in order to try and fly earlier.  There was then a chaos that resembled a stampede as all passengers ran for the nearest Southwest counter to re-book – for the flight I was supposed to be on.

What really sucked

As all of us were frantically trying to change our flights and while waiting in an enormous line, I called their 800 number and a cheerful, electronic recording told me that all of their operators were busy and could call me back – in 65 minutes.  No thanks.

I then sprinted down the terminal and and found another Southwest counter whose waiting line did not resemble a United Nations Food distribution station, there was ONE employee helping to make changes.  One.

The second Southwest employee who was there was simply watching the crowd – and was taking pleasure at telling people when they got out of the first, horrendously long line that they needed to go to the BACK of the now LONGER line because he was not booking passengers.  Dude – can you hop on a freaking computer in an emergency?  And why did you take such glee (he was smirking) as he rebuked passengers who simply got out of line to ask a question, then telling them that they had lost their place in line and were at the mercy of the already not-so-happy people to regain his or her position in line?  This included families with infants too.

By some miracle, I got on the 5:55 pm flight, inquired about my bag and was told that “protocol” was to put my bag on the prior flight (there were two hours to do it) and that it would be waiting me for in Omaha.

It gets worse

When I finally landed in Omaha exhausted and worn out, I went straight to the baggage office and was told that no, my bag was NOT on the prior flight but was “probably” on the plane I just got off of.  After waiting for 30 minutes, guess what?  No suitcase.  So when I returned to the baggage office, I was told that there were TWO more inbound flights, and bag would be sent to my hotel – and they were going to call first.  And that at the latest, the bag would be delivered after midnight.

Thursday night?  No bag.  Friday morning?  No bag.

At this point, I was really starting to get worried, principally about the life saving medications that were in my luggage.  So I called the Southwest baggage claim number and they said that my lost baggage ticket was “open,” had no idea where the bag was, and suggested that I call the Omaha airport baggage office (402-422-6162 for those of you who need it, or for YOU, Southwest management, when you read this).  Which I did.  Seven times.  Each time, no one picked up.  I left frantic messages each time and STILL have not gotten a call back.

Undeterred, I called the security office at the Omaha airport, and a nice gentlemen said he “put a camera on them” (the baggage claim people) and

I was not kidding. I needed all of these prescriptions.

I was not kidding. I needed all of these prescriptions.

said that yes, they were in the office and did not pick up his call either.  They were there, but chose not to answer the phone likely because there was going to be an angry person on the other end.

Finally, in full crisis mode, and taking matters into my own hands, I called my cardiologist’s office.  Two hours, no call back.  Thankfully, I called another friend of mine who is an M.D. and he called in everything for me.  It took three hours and haggling with the insurance company, but I got five days’ worth of meds.  And when I picked them up, I had to pay the FULL co-pay for several meds for which I only had a five-day supply, to the tune of more than $100.  A shout out to Walgreens, who were great, but that cost was something I did not need at that point.

It gets even worse

After realizing that the Omaha people were simply not going to pick up the phone (I get that you are busy, but how about calling in someone who is off-duty just to answer the phone since there was chaos?), I again called the Southwest baggage 800 number and was given the number to the Chicago Midway baggage office.  Which I called repeatedly.  Probably 20 times.  I left seven phone messages stressing that I needed my life-sustaining medications, and no one ever called back.

But this is where it gets infuriating.  Over the course of the next two days, I called the office no less than 20 times, and on FOUR OCCASIONS, a human PICKED UP THE PHONE and when he/she realized that there was a customer on the other end of the line, HUNG UP ON ME.  FOUR TIMES.  And of course, each time that I called back after being hung up on, I got the useless voicemail again.  And by the way, for those who need it or Southwest management, the number I called for Midway Southwest baggage (and got hung up on) is 773-884-3040.

Social media 911

Since I do social for living and Southwest has such a good reputation for using it for customer service, I posted three tweets, tagging @SouthwestAir and BEGGING them to help me.  Nothing.  No response, not even up until the moment that I am writing this.  I also posted on the Facebook page – twice.  And please don’t tell me about the volume of inbound messages:  you can outsource much of this and there is no industry that does more crisis training than the airline industry.  Here are just a couple of examples:

My post on Southwest's Facebook page - that they never responded to.

My post on Southwest’s Facebook page – that they never responded to.

The tragedy that was now the comedy

After being hung up on four times in Midway, I again called the Southwest baggage 800 number again and was told that they had not idea where my bag was.  I stressed the medications issue.  Nothing.  When I asked how it was that my suitcase could have a number, a bar code and TSA can tell everything that comes in and goes out of an airport, I was again told “no dice” and given no help.  Even when I pleaded about the meds issue.

It’s a sidebar to the entire story, but I came to Omaha to help a friend move.  It was 102 degrees (heat index of 110) the day of the move.  Needless to say, I had one pair of clothes (t-shirt, shorts, you name it) and I sweated so much that even the items in my WALLET got wet with perspiration.  My belt was ruined.  So I again ran to the store to spend more money on some cheesy t-shirts and let them try out on my hotel air conditioning unit at night.

The end

Or at least I hope this is the end.  The day before my departure to fly home (Sunday), I still did not have my bag.  The 800 number people told me that they had GOOD NEWS and that they had matched the bag to ME!  And it was in Chicago.  And they were sending it to Omaha on the 3:00 flight, due to land at 4:00.  I once again called the Omaha baggage office at 5:00 to find out when it would be delivered (NOW, they were answering) and was told that no, my bag was not there.  “But the guy in corporate just told me that it was definitely on the flight!”  “Sorry.”

At that point, I gave up.  I KNEW that were I to leave for DC, the bag would arrive in Omaha that day (they would take days to get the bag back to me).  I had already spent more than $200 on water, food and clothing and $84 for charging cable for my MacBook because I needed it to keep communicating – and I was borrowing everyone else’s iPhone cords to charge my phone, just to try to get some help.

The end?

I am sitting in the Omaha airport awaiting what I hope will be an uneventful flight home.  As of last night, I called Reagan National and spoke with a nice woman who assured me that my luggage was waiting for me there.  So, I may finally be able to go home.  I am unshaven, feel sore and probably look like a step above a homeless person.  But hope me and my suitcase will have a tearful reunion in Reagan National later today.

The take aways:

  1. No excuses: I get 100% that the Southwest staff was stressed and tired of being yelled at. But I never yelled.  In fact, I told several of them (in person in the airports) that I felt tremendous empathy for what they had gone through.  But most were rude and unhelpful.  You get trained for situations like this, people, and most of you could have done much better, especially since I spent five hours in Chicago and changed terminals twice because of two canceled flights and probably more than thee hours on hold tracking down my bag.
  2. Liability, anyone? I was lucky enough to track down a friend who is an M.D who could prescribe the meds, but what if I could not get them?  What if something had happened to me or I had been less resourceful?   Each and every time I called someone at Southwest, I stressed the fact that I needed to get put to the top of some priority list because of the meds.  The best that they could do was ALWAYS “message the baggage office.”  That’s it.  Sorry, but that it bullshit.
  3. Stop being jerks: There were more instances than I can name, but when I finally got on a flight here, I was waiting to board and standing next to a guy (NOTE THE WORD “STANDING”) who had JUST BROKEN HIS FOOT AND WAS IN A BOOT. He asked the Southwest ticket taker if he could please pre-board (it was obvious why) and was told – TWICE – “no.”  So you won’t let a guy with a broken foot pre-board?  I went up and talked to the ticket taker and asked him what the OFFICAL SOUTHWEST POLICY WAS for letting people with special needs board.  He had no answer, so I told him that my newfound friend would take my place in the “A” line.  And he did board.
  4. Stop nickel and diming me: Before boarding each flight and because of the experience I had leaving DC and being the last one on the plane, I paid $15 each time for “priority boarding.”  That now will come to $75.00, which I was told was not only non-refundable, but did not transfer from one flight to the next.  I had to pay to “upgrade” each time.  Seriously?  It’s not like Southwest has assigned seats, so why the heck could it NOT carry over from one flight to the next (I am looking at you, Chicago Midway)?  One would think that (again, training) that at times like this, just BENDING the rules a bit would go a long way.
  5. Don’t hide on social.  Southwest has one of the most robust social media presences in the airline industry, but they hid over these last four days.  Like I said, there is no other industry with crisis communications plans like the airline industry, and I KNOW you could have called in extra people.  Either you did and chose to ignore my pleas, or your hid behind your terminals.

I am writing this for one reason and one reason alone:  to publicly shame these people and this company.  I tried pleading.  I tried begging.  I tried persuasion.  I tried social media.  Again, I understand that an unprecedented computer meltdown doesn’t happen often, but:

  • You are trained to deal with situations like this;
  • When you FORCE me to surrender my bag and refuse to let me take my bag of meds with me, don’t lie to me when you know 100% well that my bag will never make it;
  • We are all human beings, but here’s the difference: I am paying you and you should work harder to at least help a person who was clearly in distress.  

So, shame on you Southwest.  Shame on you.





  1. Hi Mark,
    All the twists and turns of this are terrible. Here’s something I’m wondering – what if there was a STICKER, the kind that TSA approved and could be filled out AT HOME, that marks your luggage as containing medicine? The sticker marks your luggage in a way that ALL AIRLINES would have to expedite? Or it has RFID tag?

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