Sidekick’s Travel Guide: Ask a frequent flyer

You’ve taken our quiz (right?!) and know your travel personality, so let’s talk business. How do you avoid expensive flights? Deal with delays and cancellations? Duck last-minute surcharges for luggage? All hail Scott Keyes, founder and chief flight expert at Scott’s Cheap Flights, who’s here to answer all of your questions.

Bc you’re going to want all the inside scoop you can get during this particularly chaotic travel season.

This interview has been edited for length and clarity.

What’s the best way to look for flights?

“I tell people to take the way they normally search for flights and do it backwards. There are usually three steps. People decide where and when they want to go, and only then do they look at prices. By setting prices as the last priority, you’ll end up with some pretty expensive flights. So instead, take that same three-step process and flip it on its head. If you do, you can take three or four vacations for the same price as one.”

What are your thoughts on having very limited time in remote places? I go between thinking I should wait until I have more time and thinking any amount of time spent somewhere I want to see is better than none.

“If you get, say, three weeks of vacation at work, you’re going to have a choice: ‘Should I take one big three-week trip?’ Or should I take three one-week trips?’ I think if you take three one-week vacations, you get to see more places and find out which ones fit your personality. And [going to] places that are a bit more off the beaten path is how you have the most interesting and memorable trips.”

When is the best day and time to buy plane tickets?

“There are no cheaper times. Twenty years ago, when flights were first being sold on the internet, airlines would load their fares up once a week at a predetermined time, but they haven’t sold that way for years. The downside is there’s no predictable time when it will be cheapest. The upside is cheap flights are popping up all the time. You don’t have to set your calendar around it.

So even though there’s no ‘cheapest time’ to book, there are cheaper days to fly—usually Tuesday, Wednesday, and Saturday. Business travelers love to fly on Monday, Friday, and Sunday. And so those days tend to be more expensive on average than the middle of the week or the middle of the weekend.”

What’s your go-to website for knowing when to buy tickets, if you have one?

“The open secret is that the price is basically the same no matter where you book.

If you book directly through the airline, there’s a federal law that gives you a 24-hour grace period, during which time you can cancel your flight and get a full cash refund. Some online travel agencies, like Expedia or Priceline, offer their own separate 24-hour rules, but they’re not backed by law. And if something goes wrong with your flight, it’s way easier to make changes when you can just deal directly with an airline.

It’s important to differentiate where you book from where you search. It’s actually best to search on any flight search engine because that way, you can compare the prices and times for different airlines and airports. And note that Southwest flights don’t show up on any flight search engines, so you need to search directly on Southwest.com to see their fares.”

What’s the deal with hidden city ticketing? Will I actually get in trouble with airlines if I book flights that way?

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“It is very distinct not illegal, but it too against many airline policies and they’re allowed to ban you from flying with them [if you do it]. There have been instances where people abused hidden city ticketing or did it too many times and were told to either pay the difference in the ticket price or lose frequent flyer miles. Some type of ‘punishment’ along those lines.

If you decide to do it there are a couple of key things to keep in mind. Do not check a bag because that bag will go to your final destination. Do not announce your intentions to airline agents as they frown upon this type of thing. And then be prepared for the very low but not zero percent possibility that your flight could get rerouted.”

What should you do if you get bumped from your flight?

“First off, the likelihood of getting involuntarily bumped is very, very low. Airlines don’t want to force you to give up your seat; they’d rather you agree to give it up. So the upside is you can get a lot of money for doing it. Typically, it’s going to come in the form of a credit.

Flight credit is the most popular form of compensation, but it’s not the only one. Airlines essentially have a secret menu. They’re willing to negotiate with you on other things like getting you a hotel room for the night, putting you on a replacement flight, or upgrading you to business class. There’s no guarantee it’s going to happen, but it’s always worth asking.”

How should we deal with cancellations and delays during this hectic summer travel season?

“First, you want to come prepared with a backup plan. If your original flight gets cancelled, what’s the next best flight? In some cases, airlines are willing to put passengers on a competitor airline. So it’s always worth knowing a specific replacement flight [to ask for], whether it’s with the original airline or not. This is actually one of the reasons why I try to avoid budget airlines because they don’t have those interline agreements.

If your flight gets cancelled, you should stand in line to be re-accommodated. But while you’re in line, call the airline. And if the phone line tells you it’s going to be a two-hour wait, hang up and look up the airline’s international offices. All US travelers are calling the main American hotline, but you might get through sooner on an international line.

How do you avoid getting charged for luggage?

“The easiest way, rather than packing lighter, is to have the credit card with the airline if it waives baggage fees…Another option is to bring your bag to the gate because more often than not, airlines are looking for volunteers to check carry- ons free of charge. So you can pay 30 bucks to check your bag before you go through security, or get to the gate and check it for free. It’s not a guarantee because there might not be enough people on the plane to warrant that, but I’ve found that it’s something you can take advantage of especially during summer.”

Tips for traveling domestically?

“If you’re traveling domestically, search round-trip and one-way fares for the same dates. Sometimes it’s cheaper to book two one-way tickets than a round trip. This is just for domestic flights though—it doesn’t really work for international travel.”

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