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One thing I have learned about traveling in the past few years is that you can’t rely on the airlines to get you where you need to go by the time you need to get there. This is especially true when dealing with connections. Airlines have made their connections too tight, and the slightest delay can quickly throw an entire day’s operations into chaos. The best advice I can give is that if you absolutely have to be somewhere by a certain time, make a backup plan proactively. Here’s how a last-second Southwest award flight saved the day for me.
How My Travel Day Started
I was on my way home from a lovely trip to Disney World with my family. I was traveling solo, due to my work schedule. I had all of Sunday to get home, needing to be at work Monday morning. Seems fine, right? Not if you put together the unlucky combination of the Orlando airport (MCO) and American Airlines.
I try to avoid connections whenever possible. I’ll pay extra if needed — or fly a slightly less reliable airline. There were no direct flights from Orlando to Las Vegas (LAS) to be found that day, so I went with American. I snagged a cheap business-class award flying MCO–LAS with a connection in Dallas–Fort Worth (DFW). I had a mid-afternoon departure, with a 90-minute connection. Seems fine, right? Nope.
Florida weather rolled in and made a mess of the schedule early in the day. I proactively switched my connecting city to Phoenix (PHX) since I was going to miss my connection at DFW. If I got stuck there for the night, I figured I'd be close enough to LAS to grab an early morning flight to get home for work. I had a 90-minute connection again, but the weather was still causing issues long past when the skies cleared.
Springing Into Action!
As I sat in the terminal, I knew I needed more options. Thankfully, I had already done some homework in advance.
I know from experience that I can't rely on airlines to get me where I need to be on time, so I always have alternate flight options or hotels in connecting cities in mind. I scouted American’s flights for the rest of the day first and realized that missing my connection would not just strand me in PHX for the night. I also wouldn't be able to get home in time for work the next morning.
The best option in this case was making a Southwest award booking. If you don't need the back-up Southwest booking in the end, you can cancel up to 10 minutes before departure without penalty. I booked an early morning flight flying PHX–LAS. I figured I would get to PHX at some point that night with my delayed American flight, so this was the least expensive, most direct option to get me home.
This was the right move. We sat on the tarmac and in the taxi line for almost two hours in Orlando. American has been absolutely dreadful for me the last few times I’ve flown with them, and this was no exception. I missed the connection in PHX and was officially stuck. AA rebooked me for the next morning on a flight that was too late for me to get to work on time.
Figure Out The Mess, Clean It Up Later
I used an IHG free night certificate to get a room at a nearby airport hotel after American refused to offer any compensation. I told them I was making separate arrangements to get home. As for my checked bag, I didn’t want to wait for AA to find it, so I told them to send it to LAS and that I would return to the airport after work to get it. Definitely annoying, but sometimes necessary when faced with a tight deadline.
I was able to shake American down to return the miles from the flight I didn’t take, as well as 5,000 more miles for the mess of the situation. I’ll file a trip delay claim with my Chase Sapphire Reserve® to recoup the rest of my expenses. Definitely a hassle, but at least I can handle it on my own time.
Related: Best Credit Cards With Free Travel Insurance
Delays Don’t Have To Completely Ruin Your Plans
As a rule of thumb, I recommend always having backup options in mind. If you have a particularly tight deadline, proactively book that backup flight. Southwest is the best option in my opinion, because it has the most generous cancellation window. Being able to use points and have them instantly returned is ideal for this type of flight insurance policy. A last-second Southwest award saved the day for me, and it certainly can for you, too. In my opinion, it’s better to get where you need to be and then sort out the mess later — rather than trying to save points and not get to your destination on time. Miles, points, and hotel certificates can be so helpful in a pinch when you need to act quickly.
Bottom Line
I highly recommend anticipating the worst, so you can act quickly and decisively when needed. The next time you embark on a journey, remember to plan for contingencies and embrace flexibility. This can reduce stress and make your adventures unforgettable in a good way — not because of the problems you encountered in transit.
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