Where to beat winter this year and cheap flights to get you there!

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If you had to pull out a hoodie or sweater from the back of the closet this week, chances are your mind is drifting to a warm beach somewhere. Follow this impulse: start focusing on your winter getaway now.

Far too many travelers wait until winter is over to plan their winter getaways. But data shows that the best deals are at your fingertips – and the cheap flights we’re already sending to Premium Thrifty Traveler members prove it. So yes, you really should start looking to book your winter getaway.

Whether it’s a long weekend in Florida for less than $150 round trip, an unplugged retreat in the Turks and Caicos Islands with a $281 flight deal, or a week in Maui for 20,000 Delta SkyMiles or less, there are already surprisingly cheap winter fares.

When to book winter flights

Whether you’re planning a winter getaway, a vacation trip or a flight next summer, trying to choose the right time to buy your flights to get the best price can seem impossible.

The reality is that flight prices are unpredictable – they are constantly changing, minute by minute. Just like there’s no best day to book flights, there’s no hard and fast rule on how far in advance you should book. The best time to book is when you find a cheap flight… and it can show up at any time.

But now we’ve got some solid advice from Google Flights thanks to five years of data that can help you figure out the best time to book, based on when (and where) you’re traveling.

For US domestic flights, Google data shows prices are lowest 21 to 60 days before travel. On average, prices reach their all-time low for domestic travel 44 days before departure. So if you want a January getaway somewhere in the southern United States to escape the cold, that means you might find prices are at their lowest between October and December.

Well, long before that (like right now) you should set a Google Flights price alert (or a few) – and even consider booking if the price seems right. You can always rebook the flight and pocket a voucher if prices drop. Just make sure to avoid basic economy fares maintain this flexibility.

But if you don’t like what you see, set a calendar reminder in mid-October to start looking for cheap rates. And that’s only for domestic flights this winter.

If you’ve got your eyes on Mexico or the Caribbean, data from Google Flights suggests you’ll typically get the lowest prices between 37 and 87 days before departure, on average – with prices hitting their lowest around 59 days. in advance. If you’re tracking these numbers, you’ll want to start looking for your January Caribbean getaway around the end of October, with the best rates likely appearing in November before the best rates disappear in early December.

cancun beach

But where should you look? A few destinations stand out as stellar options for escaping the cold this winter.

Where to beat the winter

If only there was a service or tool that could alert you when prices drop from your home airport to some of the best winter getaway destinations…

Too cheeky? Sorry. But our Premium Thrifty Traveler The flight offer team constantly scours the world to find the best fares to nearby destinations and fares. We’ve sent out dozens and dozens of Winter 2023 flight deals to our subscribers over the past few months, but here are some highlights.

Cheap flights to Miami

Miami is a perfect option for a quick and cheap escape from winter in the northern United States. recipe for big savings for travellers.

A few miles away is a quieter string of islands that many consider paradise. The Bahamas is probably already on your list, but I bet many of our subscribers are crossing it off this winter thanks to this offer with flights as low as $266 round trip. From Buffalo (BUF) and Toronto (YYZ) to Thunder Bay (YQT) and Las Vegas (LAS), it felt like everyone had a shot at making this deal in the Bahamas (NAS).

Cheap flights to the Bahamas

But there is an even more secluded island where you can spend a winter week this year. I admit that Turks and Caicos has always seemed like a place I could never afford to visit. The just country sounds Dear. I was wrong.

Flights to Turks and Caicos

Very bad. This was the lowest fare on the latest flight deals to Turks and Caicos (PLS). But you could get there from dozens of U.S. cities for under $400 this winter, which is still a bargain for this coveted Caribbean hotspot.

The Cayman Islands take on a similar vibe to the Turks and Caicos Islands. They look expensive, but don’t have to be. These flights to Grand Cayman are the perfect winter getaway. Go spend a day on seven mile beach and let the ocean wash away your cares. Flip a $20 bill to the neighbor’s kid to plow your sidewalk while you’re away and you’re good!

Flight offer Cayman Islands

Let’s head west from the Caribbean and into Central America, where the country of Costa Rica awaits.

The best part of Costa Rica is that you can do two trips in one. If you prefer hiking through mountains and rainforests in search of rare wildlife and jungle thrills, you’ve got that in the Guanacaste region. But if you want a relaxing trip soaked in sand and sun, the West Coast beach towns (I loved visiting Nosara in 2018) are the way to go.

Just days ago, we snagged these nonstop fares to Costa Rica for less than $380 round-trip, including some of the lowest fares we’ve ever seen from Minneapolis-St. Paul (MSP) and New York (JFK).

Non-stop flights in Costa Rica

Back to the United States, where the Southwest offers idyllic winter getaways. Prepare your hiking boots and explore the mountains. Pack your golf clubs and hit the links. Pack a bathing suit and relax by the pool. I don’t care what your interests are, I bet I could plan you a great week in Arizona. And with fares as low as $117 for winter travel to and from Phoenix (PHX), you can hardly afford not to.

Phoenix Flight Deal

Phoenix is ​​landlocked, but we can also take you to the ocean. San Diego’s appeal is undeniable: it’s 80 degrees and it’s sunny almost every day of the year. Take one of these flights and improve your temperature by 80 degrees (or more…) to beat the winter.

Flight offer to San Diego

But there is something better than such cheap flights – fares that cost you next to nothing…especially to Hawaii. Even a small supply of Delta SkyMiles could get you to Maui (OGG) and back again this winter thanks to this Delta SkyMiles flash sale we sent to Premium Thrifty Traveler members just a few weeks ago.

SkyMiles Maui

Those ultra-low reward rates are now gone – jump on the next deal with Thrifty Traveler Premium!

Some of these rates are incredibly low! Our home base of Minneapolis (MSP) has earned 29,000 round-trip SkyMiles! Never seen! But what about Eugene, Oregon (EUG) or St. Louis, Missouri (STL)? A winter getaway like this is not out of reach.


You control the coming winter… but it’s time to start planning. Recent flight data and deals show it’s almost time to start booking your winter travel.

There are tons of cheap flights to the best places to beat winter. Believe me: shoveling snow is much more enjoyable when you have a sunny beach waiting around the corner.

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