Thinking Fast When Travel Delays or Cancellations Happen

Departure Delays

To help cover the operating cost of this website and provide great content, I use affiliate links in this article. I'm paid a commission if you click on, or make purchases through these links. Please read my Disclosure for more information.

I’ve become excellent at planning business trips over the years.  However, as anyone who regularly travels for business knows, delays and cancellations happen.  You need to think fast when things start going wrong to save the trip, complete the job and keep expenses in check.  If your business travel schedule is already tight, then it is more challenging when bad things happen.

Traveling for business needs planning.  You need to plan in advance as much as possible to keep expenses low, maximize your work day, and leave enough time in the schedule for sleep.   Sleeping and getting enough rest during a business trip is the most significant activity after work.  I try to plan on 10 hours in a hotel each night; one hour down time, eight hours sleep, and one hour for getting ready and eating breakfast in the morning.  I also plan on eight hours work time leaving me with only six hours travel time each day.  So what do you do when you run into troubles flying? Here’s what I did last week when flying Southwest Airlines who canceled my flight from Hartford to Detroit.

What I Did

I had a flight on Southwest scheduled to depart Hartford at 5:00 pm. It connected through Chicago Midway Airport to Detroit Michigan.   I checked in with my luggage for my flight at 3:30 pm, plenty of time to get through security, grab a bite to eat and board my plane.  The problems started for Southwest Airlines that day during my check-in when the self-serve computer terminals started going offline.  The airline representative at the check-in desk was able to check my bag and issue my boarding pass. So no one including myself thought any more about it, we assumed it was just one of those things.     How wrong we were.

Waiting at the gate for my 5:00 pm flight, 5:00 pm came and went.  First, we had an hour delay. Then we had another hour delay on top of that.  Then we had an indefinite delay.    The gate agent said a computer problem is causing all Southwest flight delays system-wide, and we should all make our connection flights.   Not so fast I thought.   Quicking thinking the issue through and the risk of not making my appointment in Detroit on time in the morning, I decided to look for another flight.  I used my Orbitz phone app and found a Delta flight direct to Detroit from Hartford departing in forty minutes.   I bought the ticket knowing I had little to no chance of retrieving my checked bag from Southwest.  Besides, I can live without my bags for a day.

Expense Considerations

In buying the ticket, I took a calculated risk in regards to my expenses.   My new ticket cost $531, my original ticket on Southwest cost just over $200; we will call it a $330 difference.   It would cost more if I was late and couldn’t finish the job before my next appointment.  I would have to push the rest of the week’s schedule back incurring additional flights costs, or book another trip costing even more if I stayed with the current flight reservation.

Also, I thought I could get a refund from Southwest Airlines for the delay, as they could not guarantee my arrival in Detroit that evening.  And I would not have to pay a hotel no-show charge.  If delayed, you can not rely on airlines paying for hotel rooms and use it to offset the no-show.  With my fast thinking, I concluded it would be cheaper to buy the ticket on Delta spending the additional money.

My Delta flight left on time, direct to Detroit.  I was able to stay at and check-in on time at my original hotel and use my original car rental reservation.  Although I didn’t have any of my luggage, I would make my appointment on time in the morning, albeit wearing the same clothes as today.


GBaggage Claimetting Back On Track With My Luggage

I tried calling Southwest Airlines to follow-up on my flight credit and luggage.  They phone system was understandably busy.  On my first call, I gave up waiting after being on hold for over an hour.  On my second and third calls, I just got busy signals.  I looked up their baggage claim offices numbers for both Chicago and Detroit and called the numbers.  I had to leave a voicemail at both locations and didn’t receive a returned call.

Fortunately, I brought a luggage tracker earlier this year from TrakDot. The information I didn’t receive regarding my bags from Southwest, I got from my TrakDot device.  Thursday morning, my TrakDot phone app was still showing my bags at Hartford Airport in Connecticut. Then at ten O’clock, I received a text message from my TrakDot device, in my bag, saying it just arrived at Chicago Midway Airport.  Then at one in the afternoon, I received another text message saying it arrived in Detroit.  A few hours later, I went to Detroit airport.  My bag was waiting in the Southwest Airlines Baggage claim office with a stressed out gentleman behind the counter.

That evening, I was able to get through to Southwest Airlines over the phone. They confirmed the cancellation of my flight from Hartford and issued a credit to my credit card for the ticket.  So, as it turns out, I made the right discussion. I kept all my appointments for the week, and the only additional cost was $330.00.

 Thinking Fast, Unexpected Travel Change Tips

  • Keep Airline and Hotel Booking Apps on your Smartphone.  You will need to book another airline ticket, or hotel stay if you’re stuck.
  • Remember you need to sleep. If traveling in the evenings and things start to go wrong, getting enough sleep is as important as keeping the next day’s appointments.
  • Only buy one-way airline tickets. Don’t buy round trip or multiple leg tickets.  If you have to make a last minute change to one of the legs on a round trip ticket or multiple leg ticket by buying a ticket on another airline and not using that leg, you will lose all the remaining legs of the original ticket costing you more.  It’s far better to buy multiple one-way tickets for a trip in case things go wrong.
  • If you can, only buy tickets on airlines that don’t charge change fees such as Southwest Airlines.
  • Don’t pre-pay car rentals. If delayed, you will lose this money.
  • Don’t pre-pay hotels stays. You will lose money if you don’t get to the hotel.
  • Do guarantee your hotel stays for late arrivals. Sometimes, hotels will give you a pass on the no-shows if you call ahead and explain the situation.
  • Fly early mornings, except Monday mornings. Early morning flights are less prone to delays and cancellations than flights in the afternoon and evenings.
  • If you check bags, use a luggage tracker. I recommend TrakDot because it automatically sends you text messages when your luggage arrives at an airport location.


Do you have any travel delay tips? If so, please share by leaving a comment at the bottom of this page.

Thank you for reading,


About Colin Robinson 60 Articles
Colin works for a high technology equipment manufacture as a senior product manager. The majority of his time is spent traveling to visit clients and to teach them in using this hi-tech equipment. He has to keep up with the latest advances in computer technology and trends and has spent over 32 years in his line of work traveling extensively. He is very passionate about sharing his knowledge and experiences with others. Read more at

Be the first to comment

Leave a Reply

Your email address will not be published.