Tips from the Experts: How to Book Flexible Travel Plans With Confidence

Tips from the Experts: How to Book Flexible Travel Plans With Confidence

TripIt is teaming up with our friends at Thrifty Traveler, a site that helps you travel more for less, to share helpful strategies for flexible travel planning.

Flexibility can take many forms when it comes to planning trips. You can travel whenever and wherever a cheap flight will take you. Or, you can change your travel dates by just a day and it can make the difference between overpaying for a flight and scoring a bargain.

But you don’t necessarily need a wide-open schedule with limitless PTO, or an “anywhere goes” mentality, to be flexible with your travel plans. Instead, use these strategies to plan a trip with flexibility built in.

Follow the flight-first rule

There’s no better way to give yourself game-changing (and wallet-saving) flexibility than reframing how you approach the travel-planning process. At Thrifty Traveler, we call it The Flight-First Rule. It’s exactly what it sounds like: Start your travel planning process by searching for flights first. In doing so, you’re giving yourself as many flight options as possible, letting the lowest prices guide you to finalize your trip.

And that’s true whether you’ve got a wide-open schedule or a narrow window to work with. Even a pinch of flexibility—say, being open to any take-off time, some lay-overs, or even flexible dates—can result in huge savings.

Let’s say you’ve got a weeklong window for that long-awaited trip to Europe next winter. Juggling PTO and home life, there’s not much room for error. In your head, you’re set on departing on a Friday and returning the following Friday.

But by heading out on a Saturday and returning a week later, you might be able to shave $100, $200, or more off those exact same flights. Multiply those savings over several tickets and it adds up fast.

This isn’t some theoretical exercise: We see these savings again and again just by shifting your travel dates by a day or two. As your willingness and ability to be flexible grows, so can the savings.

Open to flying somewhere whenever the price is right? Whether you’re heading south to the Caribbean or east to Europe, traveling during shoulder seasons like late spring or early fall can save you even more compared to the hectic peak travel periods of mid-summer, Christmas, and New Year’s Eve.

And then there’s the peak of flexibility: Letting the flight deal dictate not just when you go, but where. Maybe a trip to Chile wasn’t really on your radar, or it was simply far down your ever-growing travel wish list. But when a Thrifty Traveler Premium flight deal pops up to fly from the U.S. to Santiago for as low as $63 roundtrip, you say yes to Santiago.

Tips for putting flexibility in action

If you’ve never approached planning travel with this sort of flexibility, it might not be easy to retrain your brain to plan differently, but the savings are worth it. Here are some tips to keep in mind:

  • Use the right flight search platforms to make your flexibility work for you. The best search tools will allow you to quickly filter for the flights you want, but also help highlight the cheapest dates to travel.
  • There is no magical best day to book cheap flights, but there are cheaper days to fly. You’ll typically see the lowest prices on flights that depart and return on Tuesdays, Wednesdays, and Saturdays, when air travel demand is lower.
  • See a great deal but not sure you or your travel companion can make it work? U.S. law gives you a “book now, ask questions later” policy by requiring all airlines to give you a full refund on flights to, from, or within the U.S. if you cancel within 24 hours of booking. That should be enough time to align schedules, make sure you can get work off, and even check into accommodations or rental cars. Can’t make that cheap ticket work? Cancel it within 24 hours and get your money back.
  • Airlines are giving you even more flexibility, and you should use it. While most airlines have ended the free change and cancellation fee policies from the peak days of the pandemic, most major U.S. airlines have gotten rid of change fees on all but basic economy fares. That means you can cancel your flight for a voucher, too, if the great deal you found isn’t going to work this time.

Tip: If your travel plans change—and you don’t utilize auto-import—be sure to forward your rescheduled, canceled, or newly-booked plans to TripIt, so that you have the most up-to-date information for your trip right in the app.

How to future-proof your travel plans

Of course, there’s much more to travel than getting on a plane. And the importance of future-proofing your travel plans goes far beyond just your flights. Here are some other things to keep in mind to ensure you’re booking completely flexible travel plans (not just flights), should your plans change:

  • Consider booking refundable hotel rates. It’ll cost you a bit more, but that’s easily worth it if you need to cancel a trip to get your money back.
  • Ditto for your rental car. And given the issues with rental cars across the country this year, it might be worth locking in a prepaid rental now so long as you can cancel it down the line.
  • Planning to book a vacation rental for your accommodations? Use the search filters to display only properties with flexible cancellation policies … but always be sure to read the fine print! Just because an owner promises flexibility doesn’t mean you’ll get 100% of your money back. And almost all of them have a deadline by which you need to cancel to get a refund.
  • Thinking about tours, excursions, and all the other add-ons for your travels? It might be worth waiting until your trip draws closer to book them.

Supplemental reading: 8 Pro Tips for Booking a Vacation Rental

Whether you can adjust your plans by a day or two, travel at a different time of the year, or go wherever a cheap flight will take you, booking flexible travel plans will help you feel confident about your plans now, even if you have to change them later.

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