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Travel News Cheapest Winter Vacation Destinations

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Cheapest Winter Vacation Destinations

The cheapest winter vacation destinations happen to be some of our favorite countries to visit! We ran our data to help you discover the cheapest flight deals to book in the winter months. Check it out:

The cheapest winter/New Year vacation destinations from the United States are places worthy of exploration any time of the year. But these destinations are privy to incredible flight deals during the winter months- (along with affordable accommodations, cheap dining options, and plenty of things to see and do for free!)

Cheapest Winter Vacation Destinations: International Flights Under $500

DestinationWinter Price(Jan-Mar)Average Price Savings
Barcelona, Spain$444-$264
Paris, France$489-$198
Dublin, Ireland$479-$180
San Salvador, El Salvador$499-$145
Guadalajara, Mexico$319-$90
Mexico City, Mexico$352-$49
Reykjavik, Iceland$376-$38
Cancun, Mexico$367-$27
San Jose, Costa Rica$459-$25
San Juan, Puerto Rico$347-$8

(These prices are based on flights booked in Jan-Mar for future travel)

Looking to book a flight in December for travel this winter? We also have the data on the cheapest winter destinations to book in December for travel in January/February/March:

Cheapest Winter Destinations to Book in December Under $500 (International): 

DestinationWinter Price (Dec)Average Price Savings
Barcelona, Spain$446-$262
Paris, France$450-$238
Dublin, Ireland$476-$183
San Salvador, El Salvador$483-$162
Bogota, Colombia$436-$132

(These prices are based on flights booked in Dec for travel Jan-Mar)

Finding the Cheapest Winter Vacation Destinations Internationally: Top Tips

The most popular question: When should I book my international flights to get the best deals? 3 months in advance? 6 months? How do I nab a great flight deal to one of the world’s cheapest winter vacation destinations?

We have found most of the claims over the “perfect time” to book to be rumours.

Here’s what we do know: Book international travel as much in advance as possible to get a good deal. The earlier you book, the cheaper (generally speaking).

Cheapest Winter Vacation Destinations: Domestic Flights Under $500

DestinationWinter Price (Jan-Mar)Average Price Savings
Seattle$261-$54
New York$256-$43
Chicago $219-$40
Atlanta$220-$35
Phoenix$284-$35
Tampa$236-$33
San Francisco$277-$29
Washington, D.C.$266-$28
Los Angeles$284-$20
Denver$219-$19

(These prices are based on flights booked in Jan-Mar for future travel)

Want to book a domestic flight this December for travel later in the winter? We also have the data on the cheapest winter destinations to book in December for travel in January/February/March:

Cheapest Winter Destinations to Book in December Under $500 (Domestic): 

DestinationWinter Price (Dec)Average Price Savings
Portland$227-$81
Fort Myers$214-$74
Tampa$200-$69
Seattle$253-$63
San Francisco$245-$62

(These prices are based on flights booked in Dec for travel Jan-Mar)

Finding the Cheapest Winter Vacation Destinations Domestically: Top Tips

Unlike booking international flights, timing is important when clicking ‘purchase’ on a domestic route. The cheapest winter vacation destinations domestically involve many variables like where you are flying from, the distance of your route, local price fluctuations by season, and other factors.

Generally speaking, the cheapest deals you can find domestically will be during the winter months (right after the holidays and lasting through March).

The reason? We assume that the airlines and suppliers notice a decrease in spending habits after the holidays so they try to re-stimulate travel spending with fresh deals.

Now for our favorites. Here are our picks for the best of the best of the cheapest winter vacation destinations:

  1. Mexico
  2. Puerto Rico
  3. Paris

1. Mexico

Wherever you’re located across the continental United States, Mexico is a short, cheap flight away, making it one the easiest and cheapest winter vacation destinations. 

The Baja Peninsula is home to the always popular Cabo San Lucas and is easily accessible from the central and western U.S.  

Quintana Roo, on the Caribbean coast, has world wonder Chichen Itza, stunning beaches in Tulum, vibrant Playa del Carmen, and Lake Bacalar’s seven shades of blue. 

Or catch a flight from just about anywhere in the U.S. to the world-class museums, restaurants, and cultural sites of Mexico City

Street food isn’t only cheap here, it’s beyond delicious. Fill up on tacos and tamales for $1-$3 or check out Molino El Pujol, a small bites version of Michelin star-rated Pujol in Mexico City. 

2. Puerto Rico 

If you’re looking for an affordable vacation package deal to white sands and turquoise waters, check out Puerto Rico. One of the closest and cheapest winter vacation destinations available. 

The cost of food/drinks on the islands is affordable and the value for money on flights+hotels is great. Lovely accommodations are easy to find for under $70/night.

Don’t miss: El Yunque’s waterfalls and snorkeling on Culebra.

3.Paris

Want to see the infamous Parisian sites like the Eiffel Tower, Notre Dame, Montmartre, Versailles, Moulin Rouge…? How does seeing them without the suffocating crowds of the summer months sound? With budget flights to Europe, Paris is one of the cheapest winter vacation destinations.

Traveling in Paris is a culinary tour de force in any season. But there is something special about ducking into cozy cafes and stuffing your face with wine and cheese to escape the cold.

Christmas is big in Paris. You’ll find the city blanketed in lights, ice skating rinks spread in front of the Eiffel Tower, and Christmas markets galore.

Something to note: Be on the lookout January 8th, 2019 for ‘National Shop for Travel Day’, which occurs the second Tuesday of every year. Airlines and online travel agencies have been known to offer great travel deals on this day!