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Terrible experience with Southwest

Explorer C

I chose Southwest because my colleague recommended them. Never again! I booked return flights from San Diego to New York, flying out on Tuesday 28th and returning Friday 31st, with a brief layover in at Chicago Midway. I was travelling for business so I needed to be in New York by Wednesday.

On arrival at MDW I got a text saying the flight to New York had been cancelled and I was rebooked on a flight the following day at 4pm. This meant I would miss all of my business meetings on Wednesday. I waited in line for around 30 minutes to speak to a customer service agent, only to be told that because it was weather related Southwest wouldn’t offer any kind of compensation such as a hotel. I understand this approach is common with weather delays, but the last time this happened to me the airline (BA) paid for a hotel for the night. What was most annoying was that they refused to give me my two checked bags, despite the fact that the plane wasn’t leaving. I was told I’d have to collect them in New York the following day. If I could have collected my bags (which contained things I needed for my business meetings) I could have made arrangements to fly out that night with a different airline and still make my meetings on Wednesday. Without my bags this was pointless, so I had to resign myself to missing my meetings and spending a night in the hotel in Chicago (which I had to pay for), without a change of clothes, waiting for my 4pm flight the next day.


Wednesday morning I got another text message saying that this flight had also been cancelled. There was no alternative flight offered, so I had to call customer service. I was on hold/on the phone for over an hour and a half. In the end I was offered a flight on Thursday morning. If I took this flight, I’d not only miss all of my Wednesday meetings but several of my Thursday meetings as well. I was also concerned that this flight could be cancelled again or delayed. So I told the agent that she could reserve it for me, but that I may end up making my own way to New York because I was concerned about the flight actually going ahead. The agent said this was fine. At no point did she mention anything to me about cancelling the second leg of the trip.

I ended up flying with American Airlines that evening (which cost me an extra $300), arriving in New York at 1am. I spent Thursday in meetings. I checked my email in the afternoon only to find out that Southwest had cancelled my return leg because of a ‘no show’ from Chicago.  I assumed this was an error, so I spent another 40 minutes waiting for a call back from customer service and then 20 minutes trying to get it resolved. The customer service agent told me that the booking had been cancelled and there was nothing Southwest could do. I’d have to pay in full for a new flight. I didn’t accept this and so was given the number for customer relations. This led to another hour on hold/on the phone but with the same outcome. Because I didn’t show for the second leg of the outbound flight, they had cancelled my entire trip and refused to provide me with a flight home. As a result I’ve had to book a flight with Delta, costing another $500. In total that puts me around $1,000 out of pocket because of Southwest’s various cancellations.

Now, I understand airlines have a no show policy to prevent people skipping the second leg deliberately. But that clearly wasn’t the case here. If Southwest had actually allowed me to get either of the two second leg flights they had offered, I would have happily done so. And if the agent I spoke to on the phone, who I told my plans to, had mentioned that I needed to let them know I wouldn’t be making the second leg, I would have done that too.

I also understand that they have automatic systems in place, so when someone no shows, the computer automatically cancels the rest of the trip. Fine. But that’s where customer relations should step in, identify that this situation came about as a result of their cancellations, and correct the situation. For Southwest to not only cancel my return flights but then to refuse to provide me with a flight home is simply unbelievable. I’ve ended up paying Southwest $570 for a flight from San Diego to Chicago plus a bag of pretzels.

This is the worst experience I have had with any airline and I certainly won’t be using Southwest again.


Re: Terrible experience with Southwest

Aviator A

Sounds like you had a pretty miserable and frustrating time.


Yours is a fairly common story. A connecting flight gets cancelled. The passenger gets rescheduled, and then does not take the new flight, and the entire reservation gets cancelled.

Yes, if you had cancelled the connection yourself, your return would have been intact. Yes it would have been nice if you had been warned.


For the above reason, I almost never book RT tickets. Two one ways cost no more than one RT, although more effort is expended in the booking process.


If I were you, I'd contact customer relations to plead your case and ask for a refund. I'd also ask for several hundred$ in travel vouchers for your trouble (Not sure if you care about that since you've said that you won't fly Southwest again). The phone number is 855-234-4654.

If you get no satisfaction, you could write the CEO, Gary Kelley. You won't hear from him directly, but he'll refer to someone high enough in the food chain that you'll get a meaningful response. The address is  P.O.Box 36647 Dallas, TX.  75235.


Finally regarding the cancellations you ran into, the severe storm situation caused havoc in Chicago on the 27th. A friend flew out that evening incurring a 3 hour delay and several flights on the routing were cancelled. That also messed things up on the 28th. The weather that hit Chicago on the 27th moved to the east coast on then 28th further complicating things, casusing even more cancellations. Couple all of that with high load factors and it starts getting  very difficult to reaccomodate rescheduled passengers on a timely basis.