Five Tips to Help Smooth Air Travel Wrinkles

Oh wow. This post I wrote in December 2023 didn’t age well. Or maybe it was a sign. I don’t know. What I do know is that when 25% of your go-to airline’s fleet is grounded for safety inspections, cancellations are rough and rebooking options are less than ideal (a gross understatement). With the benefit (?) of that experience, I’ve made a number of updates to the original post.

Navigating travel snafus can be cringe-inducing even for those of us who love to fly. And it’s especially frustrating during the holidays when flights are at capacity, winter weather is in full effect, and airports are full of stressed out folks, including many who seemingly have never been in an airport or on a plane.

I’m fortunate that the vast majority of my travels have been trouble free, but certainly not all (case in point, January 2024). Since most issues are beyond a traveler’s control, planning for issues and understanding how to deal with them is key to help ensure unexpected hiccups don’t ruin travel altogether.

Before we get to the tips, though—and I can’t emphasize this enough— the people you’re likely to interact with when you have a problem are rarely the cause of the problem. And even if their mistake caused the problem, they’re human too. Calm down and treat them with kindness and respect. Be firm if you need to, but please don’t be a jerk. Kindness is free and you might just find it can be valuable currency.

With that said, here are a few tips I regularly follow for my own travels:

1. Expect (and Plan for) the Unexpected

Not to be Captain Obvious here, but it’s crucial to think about how to deal with unexpected issues before they have a chance to happen. What if I’m stuck waiting for a delayed flight? What if I’m stuck in the plane due to a delay? What if my flight gets cancelled and I’m stuck in (insert random city here)? Here are a few things I always try to include in my planning:

• This is true of ANY travel: be sure to have your essential things in a carry on in case your luggage doesn’t arrive on time. Glasses, medicine, passport … remember all of this in case you check (or gate check) luggage and it doesn’t happen to show up at the same time you do—or stays with baggage handlers in the case of a delay or cancellation. More tips to keep track of your bags are below…
• Bring extra medicine. This is a new addition to the list based on my experience in January 2024, where cancellations added 5 days to my trip. As a Kaiser member, I was able to get to their Maui pharmacy and get some short-term refills authorized just before they closed on a Saturday (and thanks to urgent care for authorizing the refill). While some blood pressure pills aren’t what I’d consider life-saving medicine, it was a reminder to bring a little extra to tide me over until I could get a refill if conditions were less accommodating, and a reminder that if you consider your medications live-saving ones to definitely bring a couple extra days worth.
• Keep some basic essentials in a carry-on bag: water, a snack (I try to keep a granola bar if nothing else), entertainment (maybe a deck of cards or a downloaded movie), and a back-up battery for your phone (see my prior post with tips). Remember: even if you make it on the plane, there’s no guarantee your food did, that cabin crew can safely offer drinks and snacks, or that the in-flight entertainment, WiFi, or power outlets work.
• Keep an eye on conditions and alerts prior to your trip. This doesn’t mean you need to stress about it (looking at you, Dad). But if you get a delay or cancellation notice before your flight, the sooner you act, the better your options will be. And if adverse weather is expected, check out your airline’s website to see if there are special instructions or waivers for changes so you might get ahead of major problems.
• At a minimum, be aware of your Plan B—especially if conditions aren’t optimal. If you book the last flight out because the fare is a deal compared to a flight two hours prior, arrive at the airport a little early. If everything goes south for your scheduled flight, you’ve increased your chances for an alternate option. And if it goes as planned, you just ended up watching planes a little longer.

Check out these additional tips on how not to get stuck during a delay or cancellation. Travel issues are bound to happen sooner or later, but they don’t have to be ruinous.

2. Know the Rules—and Your Options

While the rules and conditions airlines abide by aren’t always as customer-friendly as the flying public might want, there are certain rules airlines must follow. I’m typically of the mindset that if I understand what’s possible and what’s not, it’s easier to accept what I don’t like and to stand firm on what should be possible.

If you have an idea of what to ask for, it can help resolve some issues or at least help you feel better about the inconvenience.

• If your flight is significantly delayed or cancelled, you can often change to a flight other than the one the airline automatically chooses, if you prefer. You may be able to leave earlier, later, or connect through different cities. Sometimes, if the changes are same-day, you may be able to switch to a different airline, depending on the details. This proved futile in January 2024 as other options were already full, but the service agent did try for options on multiple other airlines.
• For a delay (other than weather, which the airline can’t control), you may be able to get compensation or vouchers for things like food (note: they’re almost always for less than the cost of airport food, but it’s something).
• Related to the note above: save your receipts. Even if you can’t connect to someone to get a voucher (or in our case in January 2024, the hotels offered via the voucher page were full), the airline might reimburse all or part of your expenses.
• Several airlines offer a discount or frequent flyer miles if your bag doesn’t arrive at baggage claim within 20 minutes. See more tips below to help prevent bags from getting lost altogether, but a little compensation is nice even when the inconvenience isn’t huge.

For some additional ideas, The Points Guy website lists a number of real life strategies to deal with delays and cancellations (such as being strategic about layovers and delay coverage with certain credit cards), as well as ideas for what to do next if a flight is delayed.

3. Advocate for Yourself

While it’s a little harder to realize in the moment, airline staff are generally interested in finding the best solution for your situation. But when the 187 other people on your flight are also waiting for help, spending extra time on creative solutions might not be the first thing on their mind. If you know what might work for you, helping them shortcut to a preferred solution can be a win-win. For instance:

• Whether via your airline’s website, or via another resource (like FlightAware or Google Flights), check out other flights and routing to be able to suggest a preferred itinerary to the airline staff. They can’t instinctively know you’d rather leave a day later and fly direct, or if you’d be willing to endure crazy routing to (hopefully) get there sooner. Or that you’d rather have a specific connection where you can spend your layover meeting up with a friend, for example.
• A flight you booked was cancelled and replacement itinerary is more than a couple hours different? You may be able to change to a better itinerary (a friend recently had his Maui-San Francisco-Chicago itinerary changed by the airline and was able to rebook to a more expensive nonstop flight at no charge). As my dad would say: the answer to an unasked question is always “no.”
• I lean into flexibility and creativity heavily when I can. It’s not always realistic, but sometimes it works out. For instance, in September 2023, the nonstop Portland-Maui itinerary I’d booked on Alaska was changed to one with flights connecting through Seattle that arrived much later than planned. I found an alternate route flying direct to Honolulu the evening prior and stayed overnight before hopping an inter-island flight on Southwest the next morning. The hotel and inter-island flight were on my dime, but the cost was acceptable to me for an extra night in Hawaii.
• Be persistent. Something better sometimes becomes available compared to the less-than-desirable option you might have been originally rebooked on. During my January 2024 trip, I checked a couple times a day to see if better flights opened up. I went from a connecting flight five days after my original, to a nonstop that day, and eventually got a nonstop flight three days after I was originally scheduled. Not ideal, but better…

4. Keep Track of Your Bags

While I generally prefer to travel carry-on, sometimes it’s necessary to check. Airlines are doing better than ever to ensure checked luggage arrives promptly with each traveler, but sometimes mishaps occur. Refer back to #1 above to remember to keep essentials out of checked bags. Besides that, here are a few tips to increase the chances of your bags arriving with you:

• Make sure your contact info is on your luggage, and duplicate it inside your bag just in case your external luggage tag gets pulled off or damaged. As an extra precaution, consider printing a copy of your itinerary and putting it in your bag in case the airline’s bag tag gets torn off.
• Distinguish your luggage from others. Even some fun stickers or a bandanna on the handle can help avoid someone else taking your bag by accident. But this isn’t foolproof—I used to have a bright silver suitcase, not exactly common, and it was still grabbed from baggage claim by someone else who thought it was hers (I eventually got it back after she got home and looked at the luggage tag to discover she’d grabbed the wrong suitcase.)
• Put a tracking device inside your checked bag (I use Apple AirTags, but other options work too). If your luggage does go missing, sharing location info with the airline can help expedite a claim, and might help you find the bag yourself. In the example above, I could see my bag was at someone else’s house, but I was fortunate that the person who grabbed it called me before I had to hunt it down.

Travel site Afar has a longer list of tips (including the ones above) to help prevent losing a bag or expedite retrieval.

5. Know Who—And Where—to Call for Help

The PointsGuy site has a detailed article about best ways to get customer service in case of an issue. It’s worth a read, but here’s my experience, at least with Alaska Airlines:

• If you’re already at the airport and can speak to someone in person, that’s always best. Especially if you’re prepared with your preferred alternates (see #2, above), the staff in the airport can make it happen in real time, or let you know other options if your preferred ones aren’t possible for some reason.
• If you’re not in the airport already, or if the lines for help there are long, calling has been the next-most successful option for me. And if the line is long, you can always try to reach customer service on the phone while you’re waiting (and chances are if one line is long, there might be a wait for both). As with in-person interaction, the benefit of a live conversation allows for creative solutions better than on-line.
• Concurrent with the above two options, or in place of them if you’re not in a place where conversation is feasible, texting the airline can be useful. It doesn’t allow for discussion the same way, but if situation is one that can be resolved with relatively simple requests (or if you’re in the air while you’re trying to resolve an issue), texting can be really efficient.
• Finally, Twitter, now X, can be a helpful resource to get an airline’s attention for issues that aren’t especially time-sensitive. Airlines will routinely move things to private messages as quickly as possible, but I’ve had luck from time to time escalating an issue via Twitter.

Unfortunately, when delays and cancellations pile up, all of the above resources get overwhelmed. If you can resolve your own issues on the airline’s app or website, that may be your best option in these situations. Otherwise, a healthy dose of patience may still be in order.

Best of luck for on-time travels in 2024 and beyond. Here’s hoping safety issues are short-lived and 2024 doesn’t repeat the meltdowns of late 2022 and early 2023…