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Flexible? Best Sites for Picking a Trip Based on Price

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Many of you—seniors, self-employed, and such—can be relatively flexible about where and when you travel. And when you think of travel, you probably look for really good deals. Fortunately, you can find several sources that will help you decide where and when to travel. A reader recently put the question to me:

“I read your article and I have a question. Do you know of any airfare website that looks for cheap fares for travelers who can travel virtually anytime but just want the lowest fare?”{{{SmarterBuddy|align=left}}}

That question involves two parts: When to fly and when to buy. If, at any given time, you know where you want to go and want to check out dates when you can fly there at the lowest fares, the websites of most big online travel agencies, aggregators, and individual airlines provide “flexible date” search systems:

  • Typically, you enter an origin city, a destination, and a date, and the site returns a grid of dates and fares for a month before and a month after the original date.
  • Cheap Tickets, Expedia, Hotwire, and Orbitz also give the option of entering a starting date and a trip duration (in days); the site returns a grid of options for up to 30 days in advance. Travelocity’s comparable system can cover up to three months in advance, but the display requires a lot of iteration and is more cumbersome.
  • Other sites, including Kayak, provide only plus-or-minus three day searches, and I couldn’t find any flexible search capabilities on Mobissimo or Vayama.

As another approach, you can sign up on several online sites—airline and agency—for bulletins on when fares drop to any given destination. Alternatively, you can place as many very low bids as you want on Priceline, varying the dates, to take “pot luck” on an airline and schedule.

Finding the best time to get the lowest fares is an entirely different matter. By now you should have heard that nobody can claim to forecast the ups and downs of airfares, except in a very general way related to the cost of oil. What we do know is that airlines periodically offer fare “sales,” and many of them are available for just one day.

Whether you know where you want to go or are just interested in good deals, your best bet is probably to subscribe to one or more sale-alert services, such as are available on SmarterTravel, that send out airfare bulletins announcing sales and other time-sensitive fare information. Many individual airlines and the big online travel agencies provide similar services. Some are general; others require that you specify a route or a destination. Be prepared to act when you see something good before it disappears.

Also, you can periodically check up on the “last-minute” postings that most big online agencies and search systems post. But you have to keep looking every few days, and there’s no point to looking until you’re about ready to travel.

If you need help deciding where you might like to go, several sites provide assistance, including Best Trip Choices, TravelMuse, and Wanderfly.

And don’t forget travel agents. A good travel agent necessarily keeps up with fast-changing airfares, as well as tours and other travel approaches. Also, most agents have a pretty good working knowledge of the world’s most popular destinations—as well as a few offbeat options—in case you need a few suggestions.

Many years ago, when airfares were far simpler and the best deals didn’t always require advance purchase, an elderly priest I knew would occasionally go to the local airport’s international terminal and ask, “When is the next departing flight?” The agent would invariably answer by asking, “Departing for which city?” And the priest would respond, “I don’t care where it’s going; I just want the next flight.” These days, you can’t be that footloose without overspending on airfares. But if you’re equally flexible, you can still find good deals.

(Editor’s Note: SmarterTravel is a member of the TripAdvisor Media Network, an operating company of Expedia, Inc. Expedia, Inc. also owns and

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