Rakesh’s travel secrets for the holidays, 2024 edition

Having flown more than two million butt-in-seat miles over the years, I’ve developed strategies for coping with the hassles of air travel. 

Holiday time is the worst. We may be full of holiday cheer, but airports are an exception, it’s even more challenging and you will be surrounded by even grumpier passengers. Many people travel only during the holidays, so there will be a lot more inexperienced travelers around.

If you don’t already have Global Entry or TSA Pre, get it right now. These can save you a lot of time in your travels with a shortcut through security. I recommend Global Entry between the two, but it often has a long wait time for enrollment. If you want travel before Christmas, you should go for TSA Pre.

The American Express Platinum card is one of several that will rebate the fee for TSA Pre and Global Entry.

Booking

  • Never, ever book through an online travel agent like Expedia or Priceline. You should use Google Flights or Kayak to find the flights you want and then go directly to the airline Web site. If you use an OTA, airlines will require you to go through them to fix anything that goes wrong. OTAs are terrible at providing service during normal times, even worse during travel nightmares that are common during the holidays. If you can’t get a hold of the OTA, most airlines will charge you an extra fee for “taking over the reservation.” That’s on top of other fees that might apply.
  • If you have to connect, be careful where you connect. Ideally, you’ll be able to get a nonstop flight. Even if it’s a few bucks more, go for the nonstop. But if you have to connect, pick the southern connection. The major airlines all have northern and southern connection points. Pick Atlanta instead of Detroit; Houston instead of Denver; Dallas instead of Chicago. I’ve spent many miserable winters at Chicago. (Unfortunately for me, warm weather connections aren’t an option.)

Before you travel

  • Download the airline app. The apps have gotten more and more sophisticated and can help you navigate the airport, rebook flights, change seats and much more. Make sure you are logged in and can see your travel plans. That way you won’t have to scramble for the information.
  • Keep your cell phone and laptop chargers in your carry on. If you suffer long delays, there’s a good chance you’ll run out of power. You might need these tools to help book your next flight. We’ve made progress transitioning to USB-C, but there are still some devices with other connectors. You don’t want to end up paying inflated airport prices for a cable. If you find that you are running out of power, look for a “power save” mode, which usually lets you eke out some more use by dimming the screen or throttling the processor.
  • Keep a pair of headphones in your laptop bag. With a laptop, headphones and Wifi, you can amuse yourself while you wait for your next flight. I spent one recent delay watching crappy television at Hulu. It won’t make your delay any shorter, but it will feel like it.

At the airport

  • It’s not about you. Don’t take flight cancellations or being involuntarily bumped personally. No one is out to get you. Running an airline is an incredibly hard business even on a good day. Add in miserable weather and high loads and a lot of people are going to be unhappy. As much as their decisions might inconvenience you, there’s usually (though not always) logic behind the decisions. Decisions take into account numerous factors including number of passengers inconvenienced, crew availability, availability of alternate flights and aircraft positioning.
  • OK, it’s a little about you. Despite these priority rules, gate agents do have some discretion to change your priority. If you’ve got a solid reason, it can’t hurt to ask. Customers who were bumped from previous flights sometimes get this kind of treatment.
  • Life’s not fair. The airline business is a business. It’s usually not first come, first served. If there’s a standby list, the 100k mile traveler who walks up 5 minutes before they start clearing standbys she will get the seat over someone who flies once a year on cheap tickets and has been waiting 3 hours. Although the rules vary by airline, priority lists typically take into account things like frequent flier status, class of service, previous inconvenience, whether you are in a connecting city, fare paid and time of check in. Chances are that if you are a non-status passenger and bought your ticket 6 months in advance, you’re more likely to get bumped because you booked a cheaper fare.
  • Check the app when things break. Usually the gate agent will tell you go to the customer service desk for help. Don’t do it. At least not before you check the app. While you walk to the counter, someone might snag that last seat through their app.
    Increasingly, airlines will automatically rebook you and send you an email, text or push notification with the new flight information. You do not have to accept what they book you on. If the revised flights don’t work, call, text, tweet with your requests. That sure beats waiting in a 90 minute line at the airport!
  • If the app doesn’t work, get on your cell phone with reservations and ask them for help. Ideally, you’ll do this while you’re walking toward customer service or standing in line. It’s a good idea to have the phone number in your speed dial so you don’t have to fumble for it. 
  • Look at the departure boards for other flights to your destination. If your flight is canceled, look to see which gate the next flight to your destination is going out from. If it’s in the next hour, high tail it to that gate and ask the agent to get on that flight. Again, be on your phone with reservations as you’re walking and standing in line. (A bluetooth headset is great for this.) If your flight is a few hours away, chances are no one is working that flight yet and you’re better off doing it yourself.
  • Look for an empty gate with an unoccupied agent. Gate agents can help you with other flights, but won’t do it if they’re busy running their own flight. Be polite, ask respectfully and you might save yourself a long wait in line.
  • Corollary: Look for an agent with gray hair. Many airlines have put GUIs on top of the more powerful reservations systems. Experienced agents often know the tricks to get the system to do things that less experienced agents can’t do.
  • If you’re a lounge member, go to the lounge for changes. Agents in airline lounges tend to know how to work the system better and are more willing to bend the rules. Unfortunately, airlines are increasingly getting rid of reservations agents at lounges.
  • If you’re not a lounge member, buy a day pass. It can be a great way to get aways from all of the noise on the concourse on a normal day, but even more so when the airport is going to hell. Of course, you also benefit from the nicer agents. During exceptionally difficult days, some airlines will stop selling day passes so that the lounges don’t get too crowded. Delta doesn’t sell them at all.
  • Be flexible. If you’re traveling to an area with multiple airports or airports within reasonable driving distance, consider taking flights there. If the change was the airline’s fault, they’ll usually pay to get you where you should’ve been. If it was weather or air-traffic control related, you’re on your own.
  • Be nice. People want to help people who are nice to them. The fastest way to get an agent to not help you is to start making demands, threaten to sue or start swearing. I witnessed one passenger in Las Vegas call an agent a “bitch” under his breath as he walked away. She called the gate he was going to and told that agent about it.
  • Call your friends. If you’re stuck and have a well-traveled friend, give them a call. I have a couple of people I can call when I get stuck to look up flight availability, hotels and other alternatives. Because they’re not dealing with dozens of other people, they can look at a wider range of options. They can give you a good picture of what your choices are. With options in hand, you become a gate agent’s friend by making their job easier. If you’re in my phone’s contact list, feel free to call me when you’re stuck.
  • Sign up for your airline’s text messaging service. Many airlines offer SMS alerts and push notifications. In normal travel, this will send you flight status information including gate assignments.
  • Don’t put too much stock in the flight status boards. When there is extreme weather and a lot of cancellations, the flight status boards are usually fiction. The times shown are best guesses and can change frequently. It’s important to know that they can also become earlier. I’ve seen flights go from a scheduled 9:30 p.m. to 12:30 a.m. back to an on time departure. It actually left at 11:00 p.m., so the people who relied on the 12:30 a.m. time missed it. If you leave the gate area, use your cell phone or laptop and check on the flight every 15 minutes or so.
  • Have alternative plans. Weather can be difficult and planes overbooked. Think about what your alternatives are if something falls through. This is going to be even tougher this year because flight schedules have less slack and there are going to be staffing shortages.

Connecting flights

  • Use inflight Wifi and check on your flight connection periodically. If your connection is delayed or canceled, you can follow the advice above to work on alternatives. Some airlines, like Delta, provide free Wifi for everyone. Even if they don’t, their Web sites are usually accessible without paying.
Unknown's avatar

About Rakesh Agrawal

Rakesh Agrawal is a 0-1 product leader. Ex-Amazon, Ex-Microsoft, as well as a number of startups. He tweets at @rakeshsfnyc
This entry was posted in travel and tagged , , , , . Bookmark the permalink.