I got caught in last week's travel mess; here's how I avoided waiting on hold to rebook my flight

It was supposed to be a short and simple trip from North Carolina to St. Louis for a TPG assignment. Instead, what I got was an up-close look at how things can go wrong when travel goes off the rails. Thunderstorms in New York on Thursday morning caused a slew of cancellations at New York's LaGuardia Airport (LGA), but the weather had a cascading effect -- though it wasn't the only cause of the problems I encountered.

Every leg of my two-day trip (which turned into three days) was either canceled or significantly disrupted. In all, I had to navigate four cancellations, two delays, one three-hour wait on the tarmac and a series of Ubers and cabs as I raced between New York airports.

It's a cautionary tale showing exactly how things can go really wrong this travel season and it serves as a good reminder about the importance of being prepared for the unexpected as you head to the airport this summer amid operational challenges faced by airlines.

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As I dealt with one disruption after another, though, I didn't spend any time on hold or waiting in line to talk to a customer service agent. I'll tell you how I avoided that. I’m sharing my experience with the hope that it helps you navigate a similar situation in case it comes up on your next trip this summer.

My planned itinerary

My assignment this past week brought me to a city I’d never had the chance to visit previously: St. Louis. The itinerary below, departing from my home airport of Raleigh-Durham International (RDU) in North Carolina aboard American Airlines looked pretty straightforward when I booked it.

Wednesday, June 15

8:07 a.m. ET: Depart RDU.

9:35 a.m. ET: Arrive at Philadelphia International Airport (PHL) for connection.

11:10 a.m. ET: Depart PHL.

12:44 p.m. CT: Arrive at St. Louis Lambert International Airport (STL).

Thursday, June 16 (return trip)

9:30 a.m. CT: Depart St. Louis.

12:59 p.m. ET: Arrive at LGA for connection.

2:15 p.m. ET: Depart LGA.

3:56 p.m. ET: Arrive at RDU.

I didn’t end up on a single one of those flights, though.

My actual travel timeline

Tuesday

I got a notification in the evening that my flight from RDU to PHL had been canceled. I used the American Airlines app to rebook. The new itinerary routed me through O’Hare International Airport (ORD) in Chicago instead. That was easy.

Wednesday

The trip to St. Louis aboard the rebooked flights went off without a hitch.

I completed my assignment in St. Louis by evening, but later that night I got a notification that the first leg of my Thursday morning return trip, from St. Louis to LaGuardia, had been canceled. I used the airline app to rebook an earlier departure, also through LaGuardia.

Thursday morning

The flight was delayed for an hour in St. Louis because of bad weather in the New York area. What I didn’t know at the time was that the storm had triggered a series of operational challenges that would affect thousands of flights over days.

My flight from St. Louis to New York eventually took off, with no concern on my part about missing my connection because I could see that the flight in New York was also delayed.

Upon arriving in New York, it became clear that the morning’s bad weather had created a mess. Terminal B was packed, travelers were clearly aggravated and finding a place to sit was a challenge.

Related: Here’s what to do if your flight is delayed or canceled

Thursday afternoon

My flight from LGA to RDU was delayed even longer than expected. After boarding quite late, the plane pushed back from the gate and began taxiing. A few minutes later, the pilot came over the intercom and informed the passengers and crew that there was a ground stop at LaGuardia caused by air traffic problems stemming from the bad weather earlier in the day.

He mentioned that there were some 50 planes looking to use the runway at that moment. Looking out the window, I could see a long line of planes.

We sat and waited. It went on so long that the flight attendants did beverage service while on the ground. Eventually, we had to return to the gate because we were approaching the maximum time a plane can sit on the ground with passengers on board, without taking off. We deplaned.

Minutes later, the flight was canceled. I went to the AA app and found there were no more options for Thursday evening. I’d be spending the night in New York. Since this cancellation was technically weather-related, I knew the airline would not be covering my stay in a hotel.

I rebooked my flight to RDU for Friday and started looking for a hotel, but there were few options available near LaGuardia. I took a $50-plus Uber ride to Manhattan to spend the night.

Related: 7 mistakes to avoid on your next trip

Friday

I headed to LaGuardia in the morning — another $50-plus Uber ride.

I had just stepped out of the Uber and walked into the terminal when I got a notification that the flight was canceled. I went to the app once again and found there were no flight options available until Sunday.

With extremely limited options out of LaGuardia at this point, I heeded the advice of TPG’s aviation team, hopped in a cab and headed to John F. Kennedy International Airport (JFK) to see if I could standby for the 12:48 p.m. flight to RDU.

It was noon when I walked into JFK Terminal 8. Thankfully, there was no line at the American Airlines priority check-in counter. I gave the agent my confirmation number, but there was no trace of my reservation in the system now! No sign of my reservation in the app either.

It took a few minutes of searching, but it was found and that problem was resolved. I got on the standby list.

I headed to security, which I got through in seconds (thanks, TSA PreCheck). When I got to the gate I saw that I was right at the top of the standby list, which I cleared moments later. That was a relief. The flight from JFK to RDU took off on time, and I was on the ground in North Carolina shortly after 2 p.m.

What you should know for your travels

In recent months, I, along with my TPG colleagues, have written about the ways in which travel can get disrupted as travelers return to the skies. It’s an entirely different thing to experience how things can snowball. I still have no idea what caused the first flight cancellations on my trip — the ones I was easily able to navigate by rebooking.

Few travelers are immune to such a scenario this year as airlines face operational challenges brought on by a combination of staffing, weather and air traffic control problems that had U.S. Secretary of Transportation Pete Buttigieg meeting with airline executives on Thursday; the same day my itinerary — and those of thousands of other travelers — got thoroughly upended.

Some of these problems can come without an easy solution, no doubt. As I sat in seven cabs or Ubers, five airports, five planes and one hotel over the three-day period, I began keeping a running list of what tips might be useful to other travelers if they run into similar situations this summer.

Related: Avoiding long lines at the airport and during your travels

1. The airline’s app is the often quickest and easiest solution

As I mentioned, when my flights out of Raleigh-Durham and St. Louis got canceled, I was able to pull up the airline app and rebook myself on another flight. I was able to do this within seconds. This is an option you’ll have with most airlines.

While some situations require human interaction with an airline representative, in a lot of cases you can bypass the multihour waits on the phone or the long lines I witnessed at countless customer service desks last week. Using your app you may be able to book yourself an entirely new itinerary, choose your seat and download your boarding pass with just a couple of clicks.

2. While on the app, lock in a flight, but then keep looking

Depending on the circumstances and the type of ticket you booked, you may be able to make multiple changes to your itinerary when your flight gets delayed or canceled. This can be handy if the first option you find isn’t ideal. My strategy was to book something that would at least get me where I needed to be in a reasonable time frame. Then I’d refresh the page and spend a little more time searching for new or different options that appeared. Keep in mind that as other travelers rebook, seats on planes will open and close pretty rapidly, so your choices may continually change.

Now, this isn’t to say you’ll always have great options. Particularly when you see mass disruptions like LaGuardia had on Thursday and Friday where so many travelers were trying to find empty seats, the choices can be extremely limited. There were moments after my Friday flight out of LaGuardia got canceled when I was seeing no options in the coming days.

As former airline executive and aviation consultant Robert Mann explained to me on Friday, when this happens, "There’s very few places to put people” at that point.

3. Consider in advance what you would do if you got stuck — particularly in your connecting city

I had no plans to spend the night in New York City, but that’s where I ended up Thursday night. Sometimes when there's a layover on your flight, you don’t think too much about the location beyond the airport concourse. But considering the current air travel operational issues, there’s always a chance you could end up in a connecting city for a day or more.

This can also mean you'll incur unplanned expenses for food, lodging and travel to and from the airport. It could be a reason to consider a travel credit card that has protection for these unexpected situations. Some of those cards can also get you airport lounge access for a break from the chaotic terminals, though on days like Thursday and Friday, those lounges were likely quite full.

4. Keep an eye on the incoming plane

Whether you’re using a browser, the departures and arrival board at the airport or an airline app, there are plenty of ways to keep an eye on the plane that will ultimately carry you to your destination.

When I was delayed in St. Louis, the app offered me the chance to rebook the second leg of my trip to RDU. The system seemed to fear the current delay would cause me to miss my connection. I was inclined to make the suggested change at first, but then I checked the incoming plane for the flight from LaGuardia to RDU and saw it, too, was significantly delayed. I’d make the flight in plenty of time. Of course, that turned out to be an understatement after the flight got delayed and canceled many hours later.

You can even go online and see, for example, that your plane on a flight out of Dulles International Airport (IAD) will be coming from Newark (EWR) but that it is currently delayed at O’Hare (ORD).

“If you do see that, it’s time for your hair to stand up a little bit and think about what your options may be,” Mann explained. It’s not to say you’re doomed, but it could be a good way to start planning ahead.

5. Search for the silver lining along the way

As Mann pointed out to me when I spoke with him on Friday just after landing in North Carolina, these types of disruptions for travelers — particularly those who have saved money or points, planned the trip and taken off time from work — can be quite devastating.

When it comes to those stuck for days on end, he said, “That just means their trips are ruined.”

It’s a sentiment with which I certainly empathize, though I hope travelers can find some ways to still enjoy themselves along the way.

I’ll start. On one of my rebooked flights on this trip, my upgrade cleared when it didn't look like that was going to happen on the original flight. It was my first upgrade since crossing into American Airlines Gold status.

I also got to visit New York City for the first time in more than a decade.

While I didn’t get to see much of the city, I got to check out Hyatt's beautiful Andaz 5th Avenue Hotel in Manhattan, a stay punctuated by the property’s incredible breakfast offerings.

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(Photo by Sean Cudahy/The Points Guy)

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These types of travel disruptions are a reality this summer as airlines and the travel industry attempt to meet surging demand. A little preparedness and patience could go a long way this summer toward navigating situations like mine.