May 19, 2024

You’re the Boss: Web Tools for the Flexible Flier

Tech Support

I’m one of those people who can get a little carried away when trying to find a slightly better or cheaper flight or hotel for a business trip. Kayak is my obsessive tool of choice — I haven’t found a site that matches it for comprehensive coverage of airlines and hotels and for its ability to play with variables.

Later in this post, I’ll mention another site that could come in handy for managing online travel arrangements you make through Kayak and elsewhere. But first, here are some of the techniques I use to take maximum advantage of Kayak’s bargain- and preference-hunting power — along with a few suggestions from a savvy entrepreneur.

Pick your airports. An odd glitch on Kayak is that sometimes you’ll turn up great fares to a city when you specify a single airport — fares that won’t show up if you allow searching at multiple airports. That shouldn’t be the case, but there you go. (My wife discovered this trick — I had confidently maintained, expert that I am, that it was a waste of time to plug in airports one at a time, until she showed me the results.)

Cross-check hotel reviews. Kayak will always turn up what look like great hotel bargains. The problem is that while airlines are more or less alike, hotels can be as different as night and day. The overview and the “star” rating system don’t tell you much. You need user reviews to have a sense of what you might be getting yourself into. Kayak will give you access to some reviews, but usually not enough. When I find a promising hotel deal on Kayak, I hit TripAdvisor’s more extensive and reliable collection of user reviews for a cross-check.

Book direct. When I find a good flight or hotel on Kayak, I usually go to the airline or hotel Web site and run the search again. Occasionally, doing so will turn up additional flight or room options, plus there can be advantages to dealing directly with an airline or hotel if you have to make changes or cancel — for example, some travel sites will demand full nonrefundable payment in advance, while the hotel site and even some airline sites might let you hold that same reservation for some time without a deposit. (More on this below.) Usually the same deal Kayak found will be available on the airline or hotel site, but if it isn’t, you can go back to Kayak and book it through the travel sites Kayak suggests.

Learn to love layovers. Most people think of layovers as one of the trials of flying, something you do because a nonstop isn’t available or is too costly. I see a layover as an opportunity to work in a second mini-business trip, or just a micro-vacation — and to save money.

The simplest way to get Kayak to help is to do a regular round-trip search and then on the results page click on “flight quality” (on the left) and then on “layover duration” and see if you can extend the duration long enough to allow you to run into the city. Try different layover cities you might be interested in hitting by clicking the “airport” button on the left and then clicking on “layover airports.”

Some cities, including Boston, San Francisco, Washington (Reagan National), Baltimore and London have such reliable and speedy rail connections from the airport that you can squeeze a one-hour business meeting into a three-hour layover even during rush hour. To spend more time at the layover city — and sometimes save even more money — click on the “more options” link near the top of the results page. Then click on “multi-city.” Plug in your dates and cities again, but this time include the layover city you’re interested in, giving yourself a whole day or even an overnight at your stopover. Not only is this likely to turn up better extended layover options, it will often turn up cheaper fares than the regular round-trip search.

I was pretty sure Jason Freedman (no relation), co-founder of flight-delay-predicting service, would be good for a few online bargain-hunting tips, and I was right. (A few months ago I wrote about Jason’s advice not to be a stealth start-up.) Here they are:

Use your cancel power. It turns out that all major online flight-booking services allow you to cancel any flights you purchase through midnight the next day, as do the airlines themselves. They don’t make it easy for you to know this, Mr. Freedman said — I didn’t know it — and you might have to call them to cancel, but you can cancel, and with no penalty. That means you can grab that attractive flight deal in the morning, and then monitor prices for the next 36 hours to see if there’s a drop, as there often is. That’s particularly handy if you’re buying on a Monday, Mr. Freedman said, because prices often fall on Tuesday. (Exceptions: airlines such as American that usually allow you to hold a reservation until the next day instead of having to purchase it won’t let you cancel after you purchase. Also, flights that are part of a travel package often can’t be canceled through this policy.)

Check seating charts. Never mind picking a good seat, Mr. Freedman said. Check the charts to see if there are more than 15 seats left on your prospective flight. If so, you might want to hold off on buying, because prices are more likely to drop than go up as you get closer to the flight date. The best place to monitor seat availability is with Expert Flyer, Mr. Freedman said, though the service will cost you at least $4.99 a month. Airline seating charts usually won’t show all available seats, he added, and booking services like Orbitz tend to show even fewer, but just knowing that there are more than a few seats available is often enough to suggest that you’d be safe holding out.

One advantage to using Orbitz or Expedia to find your flights and hotel is that these services will create a neat itinerary for you. But if you want the flexibility of Kayak, you’re on your own creating an itinerary. That means that once you’ve booked your five flights from two different airlines, and your three different hotels, not to mention car, train and dinner reservations, you can spend another half an hour copying the details into a self-prepared itinerary. And let’s hope you don’t have any typos in flight times, hotel addresses or confirmation numbers. Or you could use Tripit, a service that makes it easy to gather the scattered results of your brilliant travel machinations automatically. After you set up a free account with Tripit and give it the dates of a specific trip, just book your flight or room or car or whatever, and then forward the inevitable confirmation e-mail notes to Tripit, which will then, in theory, pull out the key information from the note, and stick it in your itinerary. Tripit will even search through your Gmail account, if you let it, to find the information on its own.

I’ve just started using Tripit, and so far have found that it seems to work reliably. Personally, I plan on continuing to take a close look at the results until I’ve seen Tripit handle many, many bookings flawlessly. I note the service allows you to rate how good a job it did transferring the data from a note into the itinerary, suggesting that it doesn’t always get it right (which is to be expected given the variety of booking services out there).

Now excuse me, I’m actually on a trip right now, sitting in a Dunkin’ Donuts, and I have to figure out what train will get me to my next destination. Too bad Kayak doesn’t do trains. But good thing Google Maps does.

You can follow David H. Freedman on Twitter and on Facebook.

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