5 Winter Destinations With Cheap Flights From the East Coast

Winter Destinations With Cheap Flights From East Coast USA
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Winter is my least favorite season. I could live without New England’s icy roads, flu shots, and heavy coats. Nevertheless, despite all the hassles, winter is my favorite travel season. Over the past few years, I’ve traveled inexpensively to many winter destinations around the world.

Two years ago I traveled to Dublin, Ireland and last year I traveled to Cancun, Mexico during winter. This year I vacationed in Guadeloupe in the Caribbean. I also have upcoming weekend trips planned to Chicago and Sweden.

Ireland is incredibly green – Cliffs of Moher in January!  

Why Travel During Winter

Cheaper Flights, Lodging, and Rail  

Traveling during winter is an economical way to see the world. In winter, enjoy discounts on flights, hotels, and train tickets.

Winter is my favorite season to travel because flight deals are plentiful. You can find incredible deals to many destinations across the U.S. and around the world. This is especially true if you’re flying from the East Coast.

Fewer Crowds  

Since most travelers like traveling in warm weather, take advantage of the off-peak season. During the winter months, you can expect fewer crowds at even the most popular destinations around the world.

How About The Weather

Can you tell that this was my only beach day in Cancun, Mexico?

The weather isn’t always ideal in the winter. Here are few examples of both the good and bad.

Because of the rain, I had to cancel my parasailing excursion in Cancun, Mexico. I ended up losing two beach days in Cancun.

On the other hand, January in Dublin meant that I had one of the most breathtaking, unobstructed views of the ocean from the Cliffs of Moher. I practically had the cliffs to myself!

With winter travel, it’s all about perspective. You may face some weather-related setbacks, but the rewards are worth it. Trust me, don’t stress out about the weather.

Best Dates to Travel in Winter


Look for flight deals three weeks after Thanksgiving. If you can, avoid traveling the week of Christmas and New Years. But don’t fret, those price spikes will come crashing down soon after the holiday season.


Look for cheaper flights between January 4th and Martin Luther King Day (changes every year). Many destinations also offer discounted flights for the entire month of January.


The month of February is another great time to score cheap flights. Avoid traveling a few days before and after Valentine’s Day. Travel before prices increase for spring break in March.

Even if you don’t get to travel in February, you can still gift yourself an unforgettable experience in your hometown, especially for Valentine’s Day. Couponbox, a free coupon portal that provides coupons, shopping guides and more, recommends going on a nature walk or a rock climbing adventure.

I’ve taken their advice and gifted myself a beginner tango workshop (that transports me to Argentina) and a Valentine’s Day yacht cruise in New York City.  

For more date specifics, Ginger on the Go does a phenomenal job detailing and color coding the best and worst weekends to travel on a budget in winter.

Winter Destinations from The East Coast

Here are my top picks for winter destinations with cheap departures from the East Coast. Also, check out how to find cheap flights departing from the U.S.

Stockholm, Sweden  

Ever thought about visiting the capital of Sweden? Now’s a great time. Traveling to Stockholm from the East Coast has never been cheaper!

Norwegian Air Shuttle offers long-haul, low-cost flights to Stockholm from New York City. Back in June, I booked a round-trip ticket to Stockholm for $276 USD for dates in February.

For more ways to save when booking with Norwegian Air Shuttle, use this simple Norwegian Air Shuttle currency conversion travel hack.

Related: Sightseeing Stockholm: Postcard Worthy Sights To See 

San Juan, Puerto Rico

If you’re looking for a Caribbean island getaway, consider flying to Puerto Rico. The Isla Verde hotel strip has plenty of beach bars and casinos or head to the charming Old San Juan to visit the 500-year-old El Morro Fort.

I’ve found round-trip flights from Baltimore ($215), Boston ($218), New York City ($191) and Washington D.C ($200) for dates from December to March.


The start of a 4-hour hike to the top of the La Grande Soufriere in Guadeloupe. 

Looking for more amazing winter destinations in the Caribbean? Guadeloupe will capture your heart.

I loved Guadeloupe’s rich French Caribbean culture, delicious cuisine and the lush green mountainous landscape of Basse Terre.

For as cheap as $49 USD one-way, you can fly to Guadeloupe with Norwegian Air Shuttle. I stayed at Caraibes Bonheur in Deshaies which caters to budget-conscious travelers.

I’ve found one-way flights from Baltimore ($49), Boston ($49), Fort Lauderdale ($79) and New York City ($79) for dates from December to March or April.


The French Caribbean island of Martinique is on my list!

With pristine beaches, rainforests in the North and black sand beaches, Martinique is easily accessible (and affordable) from the East Coast.

For as cheap as $49 USD one-way, you can fly to Martinique with Norwegian Air Shuttle.

I’ve found one-way flights from Baltimore ($49), Boston ($49) and New York City ($79) for dates from December to March or April.

Cancun, Mexico 

Leave your winter coats behind and escape to Cancun, Mexico this winter.

Spend a day exploring the Yucatán Peninsula and the ancient Mayan ruins at Chichen Itza or enjoy the nightlife at one the hottest nightclubs in town.

I’ve found round-trip flights from Atlanta ($265), Dallas ($181), New York City ($258) and Philadelphia ($260) from December to March.

What are YOUR favorite winter destinations? Let me know in the comments below!

12 replies
  1. mytravelmoment says:

    Great tips! On the top of my list I would put Norway or Ireland :) Caraibes could be a good option for some last minute trip !

  2. The Family Voyage says:

    We really loved Spain in the winter! Barely any tourists and the whole country is beautifully lit from the beginning of December until early January.

  3. Sandy N Vyjay says:

    Those suggestions are great. I would definitely look forward and plan my travel well in advance to suit the off season time and rates. The destinations are wonderful as well. For me Sweden looks the most alluring.

  4. Chantell says:

    I am exactly the person who needs these kind of articles – I hate the cold and have spent most of the European winter in the warmer cities ha ha. Cancun is a good destination – especially isla mujeres or Isla Holbox. Also we stayed downtown, rather than in Zona Hotelera which gave us such a different insight into Cancun.

  5. Candy says:

    Such great suggestions. I always try to travel off peak season to score the best rates and to avoid the crowds. Even with airline points/miles, it’s easier to get business class seats for the same amount as economy class :)

    • Danielle Desir says:

      This is something that I need to look into more. I have a ton of banked miles. I want to look into using them wisely, especially if I can get a business class seat with the same amount of miles!


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