The Best Time to Plan Your Winter Vacations

In a Nutshell: The best time to plan winter vacations, particularly for Christmas and New Year’s, is from July until Labor Day, September 4th. For Thanksgiving, book discounted flights in September and October, and for Christmas, aim for October and November.


  • Start looking for Christmas flight deals in July, with the best window closing by Labor Day, September 4th.
  • For Thanksgiving, the prime time to find discounted flights is in September and October, while for Christmas, it’s October and November.
  • Be cautious with last-minute bookings as holiday travel is trending 11 to 12 percent more expensive than the previous year.

Winter Vacation: When is the Best Time to Book?

As the shimmering heat of summer begins to fade, many are already turning their thoughts towards winter vacation plans. 

Jason Wheeler, a renowned news anchor, editor of Right on the Money at WFAA in Dallas, sheds light on the best strategies for holiday travel booking in his latest discussion.

The Ideal Time for Holiday Flight Shopping

According to Wheeler, the best time to start hunting for Christmas flight deals begins in July.

Information from (formerly Scott’s Cheap Flights) suggests that the window for snagging deals for Christmas and New Year’s travel starts to close by Labor Day, September 4th. 

This insight is crucial for those aiming to avoid the rush and the hike in prices as the holidays near.

Taking Chances with Last-Minute Bookings

However, Wheeler also points out an alternative approach. Data from, analyzing 11,000 flights, indicates that while August should be avoided for booking winter holiday travel, there are still potential discounts to be had. 

They predict the best time to find discounted Thanksgiving flights is in September and October, and for Christmas in October and November.

Yet, travelers should be aware that holiday travel is trending 11 to 12 percent more expensive compared to last year.

Google Flights Guarantee Feature

A noteworthy tip from Wheeler is Google Flights’ new guarantee feature. 

If you book a flight with the guarantee badge, Google continues to monitor the fare, offering a refund if the price drops significantly. This feature adds an extra layer of assurance for travelers looking to economize.

Flexibility in Flight Schedules

Wheeler emphasizes the importance of being aware of airline schedule changes. Booking early, which is often the best time, might lead to receiving notifications about changes in flight times.

This situation often grants passengers the right to alter their flight plans or get a refund, even if the original booking was non-refundable. 

This policy varies by airline, with some offering flexibility for changes as minor as 30 minutes, while others require a shift of four hours or more.

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