I’m supposed to fly southwest tomorrow

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Southwest Airlines is in the midst of an unprecedented collapse, canceling more than 2,000 flights a day with no certain end in sight. Like millions of Americans, I have a southwest flight on the books this week that looks to be in jeopardy. Here’s what I do to protect myself and make sure I get where I need to go.

Long before any hint of trouble I booked a South West positioning flight to New York City-LaGuardia (LGA) in order to hop on a transatlantic flight for one simple reason: Southwest was the cheapest option… by hundreds of dollars. I’m not afraid to fly southwest. In fact, I really like the simple and flexible low-cost carrier – especially for a ski vacation like this, because Southwest lets me check my ski bag for free. Everything made sense.

Like many travelers, I locked this flight months ago… and now it looks like I’m going to get caught. Since Christmas Day, Southwest has canceled more than 7,000 flights, nearly two-thirds of all of its operations. And the airline has suggested that these mass cancellations will continue at least until the end of the week. My chances of taking off with Southwest tomorrow are not good…

For most travelers this week, the easiest option is to cancel your travel plans, wait for Southwest to cancel, and get a full refund. But I’m determined to get to New York. Here’s what I do to make sure.

Monitoring my flight status

From what we’ve seen and heard over the past few days, Southwest’s system is so strained that travelers aren’t even notified when their flight status changes in many cases, requiring you to find out for yourself. -even.

I have Southwest’s flight status tracker on my phone and continually updating today to make sure my flights are correct. Right now they are (*Knocks hard on wood*).

But if we have learned anything from this ordeal, it is that we must also take matters into our own hands. Besides tracking my flights through the southwest, I also use a few other tools. I am a fickle Pro user, so the flight tracker app will send push notifications to my phone if anything about my flight changes. I’ve had a few tail number change notifications already, which just means the actual plane I need to fly on has changed, but nothing in terms of cancellations yet.

Pro steering wheel

All is well so far too.

Finally, I have a tab for Aware of the theft open, which also has up-to-date flight data for me.

Aware of the theft

Unexpectedly, Flight Aware agrees that my flights are not canceled yet.

I’m a bit superstitious, so writing this post gives me goosebumps. But even with a lot of green on the board for my flights tomorrow, I need a backup plan.

Provisional flight reservation: the emergency plan

Yesterday, when things were starting to get particularly bad for Southwest, I turned on the old Google Flights machine to find an emergency way to get to New York.

From Minneapolis (MSP), there weren’t too many options left and there were exactly no affordable options. Still, this was at the start of the Southwest Collapse, so there were far more and cheaper options than there are today. As of this writing, there’s nothing in NYC for less than $500 in savings on Wednesday or Thursday.

Although I really didn’t want to shell out $500 for a one-way positioning flight, I had Delta SkyMiles in my account, so I used them to purchase an interim flight to New York on Thursday morning just in case Southwest Axes my current projects. The new flight booking cost me an ungodly amount of SkyMiles… like, really bad guys…

Ikon vs Epic Ski Pass Guide

I hope Southwest will operate my flights normally and then I can cancel this main cabin SkyMiles booking and have those miles redeposited to my account.

But otherwise, I have a way to make my Thursday night flight out of New York. Until I check in for my Delta flight, I will be allowed to cancel for a full refund of SkyMiles and taxes and fees because it’s a Main Cabin fare. Fingers crossed, I can do it.

Know my rights

Thus, the walls are closing in on my flights to the southwest. My flights are statistically unlikely to operate tomorrow, so I need to know how to get a refund if and when they cancel my itinerary.

For one thing, Southwest has issued a system-wide change waiver for all flights through January 2, which means you can rebook yourself on any other flight with no change fees or price difference. That, of course, is easier said than done given how few seats are available in Southwest’s network right now. If you can, your best bet is to push your booking back until 14 days before your original flight (which is the maximum allowed by the waiver).

Landing of a Southwest Airlines plane

If you cannot, you will need to request a refund from Southwest if they cancel your itinerary. You can do it on Southwest website by entering your confirmation number as well as your first and last name.

Remember: If Southwest cancels your flight, you are entitled to a refund as required by law. Be sure to request your refund as soon as possible after your cancellation.

Additionally, you could potentially be reimbursed for certain other travel expenses incurred as a result of cancellations between December 24 and January 2. You have to go through this contact page on the Southwest website. It is important to note that Southwest does not have to honor your requests if they deem them unreasonable. Criteria for “reasonable requests” are not listed, but Southwest’s site says it will honor reasonable requests for hotel, meal, or alternative transportation reimbursement.

Trip delay insurance

There are four travel rewards credit cards that offer some sort of trip delay or cancellation insurance.

Some of these cards have better coverage than others, but you must have booked the flight with one of these cards to be eligible for coverage. Even if you used Southwest miles to book, paying taxes and fees with one of these cards should guarantee you coverage.

We have a complete list of all these insurance policies on our website. I recommend checking it out to see what you might get in return for your Southwest troubles this week.

In my case, I booked this flight with the Platinum Card from American Express, which means I have trip cancellation and interruption coverage up to $10,000 for my issues on a ticket. round trip under the “bad weather” clause of the cover.

Here’s the caveat, though. This coverage on the Platinum Card is only available for return bookings – or, in some cases, open-mouthed flights. When I originally booked this fare it was for a return ticket to and from LGA. Since then, however, I found a better return option and canceled the return for good. So where does that leave me when it comes to coverage? I’m not really sure. I have a receipt for a round trip and Southwest has all that money (I got e-credit after I canceled the return, not money), but I no longer have the return on my itinerary.

Hopefully you and I won’t have to use that coverage this week, but it’s worth checking whether or not you have travel rewards credit card coverage in your wallet.

Worst case scenarios

If a tentative flight reservation is too expensive or unavailable, you should exhaust your options.

That could mean packing up the car and hitting the road. If you can take your car, great. If not, it’s time to look at some cheap car rental options.

AutoSlash is our favorite tool to find the best deal on a rental car, especially on short notice.

auto slash

If you are in a place with Amtrak service, you should look to see if you can also take a train to your destination.

Leave nothing to chance. It’s time to dig into that travel tool bag and make it work!


I have an untimely southwesterly route tomorrow so I’m taking a number of steps to make sure I always get where I’m going because the airline is canceling two-thirds of its flights over the next few days.

By closely tracking my flight, booking a tentative itinerary, knowing my rights, and reviewing my travel insurance protections, I’m doing the best I can in a bad situation.

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