Sidekick Travel Guide: Ask a Frequent Traveler

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You’ve taken our quiz (right?!) and know your travel personality, so let’s talk business. How to avoid expensive flights? Manage delays and cancellations? Avoid last-minute baggage surcharges? All hail Scott Keyes, Founder and Chief Flight Expert at Scott’s Cheap Flights, who is here to answer all your questions.

Because you’re going to want all the 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 search for flights?

“I tell people to take the way they normally search for flights and do it in reverse. There are generally three stages. 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 will end up with quite expensive flights. So instead, take that same three-step process and flip it. If you do, you can take three or four vacations for the same price as one.

What do you think about having very limited time in remote locations? I oscillate between thinking I should wait for more time and thinking that spending time somewhere I want to see is better than none.

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

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

“There are no less expensive periods. Twenty years ago, when flights were first sold on the Internet, airlines loaded their fares once a week at a pre-determined time, but they haven’t sold that way for years. The downside is that there is no predictable time when it will be the cheapest. The advantage is that cheap flights appear all the time. You don’t have to set your schedule around this.

So even if there is no “cheapest time” to book, there is are cheaper days to fly, usually Tuesday, Wednesday and Saturday. Business travelers love to travel on Mondays, Fridays and Sundays. And so these days tend to be more expensive on average than the middle of the week or the middle of the weekend.

What is your go-to website for 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 with the airline, federal law gives you a 24-hour grace period, during which you can cancel your flight and get a full cash refund. Some online travel agencies, such as Expedia or Priceline, offer their own separate 24-hour rules, but these are not guaranteed by law. And if something goes wrong with your flight, it’s much easier to make changes when you can simply deal directly with an airline.

It is important to differentiate where you book and where you search. It’s actually best to search on any flight search engine, because that way you can compare prices and times of different airlines and airports. And note that Southwest flights do not appear on any flight search engine, so you must search directly on Southwest.com to see their fares.

What’s wrong with the Hidden Cities ticket office? Will I have problems with the airlines if I book flights this way?

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“It’s very distinctly not illegal, but is against many airline policies and they are allowed to ban you from flying with them [if you do it]. There have been cases where people abused the city’s hidden ticket office or overdid it too many times and were told to pay the difference in the ticket price or lose frequent flyer miles. A kind of “punishment” in this sense.

If you decide to do this, there are a few 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 such things. And then be prepared for the very small but not zero possibility that your flight will be rerouted.

What should you do if you are kicked out of your flight?

“First of all, the likelihood of getting knocked down unintentionally is very, very low. Airlines don’t want to force you to give up your seat; they prefer that you agree to give it up. So the advantage is that you can get a lot of money doing it. Typically, this will take the form of a credit.

Flight credit is the most popular form of compensation, but it is not the only one. Airlines basically have a secret menu. They’re willing to negotiate with you about 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 this will happen, but it’s always worth asking.

How should we handle cancellations and delays during this busy summer season?

“First, you want to be prepared with a back-up plan. If your original flight is canceled, what is the next best flight? In some cases, airlines are willing to put passengers on a competing airline So it’s always useful to know a specific replacement flight [to ask for], whether with the originating airline or not. That’s actually one of the reasons why I try to avoid budget airlines because they don’t have these interline agreements.

If your flight is cancelled, you must queue to be relocated. But while you’re on the line, call the airline. And if the phone line tells you there’s going to be a two-hour wait, hang up and look for the airline’s international offices. All US travelers call the main US hotline, but you might switch to an international line sooner.

How do I avoid being charged for baggage?

“Easiest way, rather than packing lighter, is to have the credit card with the airline if they are waiving baggage fees…Another option is to bring your luggage to the gate because the most often, airlines are looking for volunteers to check the transport – free of charge. So you can pay $30 to check your bag before going through security, or walk to the gate and check it for free. It’s not a guarantee as there may not be enough people on the plane to warrant it, but I’ve found it’s something you can take advantage of, especially in the summer.

Advice for traveling within the country?

“If you are traveling domestically, look for round-trip and one-way fares for the same dates. Sometimes it’s cheaper to book two one-way tickets than a round trip. It’s just for domestic flights, it doesn’t really work for international travel.


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