The Fastest Way to Snap Up Winter Travel Deals

As a resident of the gray, frigid Midwest, booking cheap winter vacations is a passion of mine. Sometimes you just need to get the heck out of the house and fly far, far away. I’ve taken some of my happiest vacations during the winter.

Winter travel deals are often easier to find than you might think. Good winter travel doesn’t have to involve going to a beach or taking a cruise. You can often find great winter travel deals if you want to visit big cities, travel to other countries, or choose an all-inclusive vacation package at a resort.

Let’s look at two fast, easy strategies you can start using today to help book winter travel deals.

1. Start with Google Flights and Skyscanner

Saving money on winter travel often starts with booking cheap flights. If you can get a cheap plane ticket to a warm-weather climate or a big city you’ve been longing to visit, that will often make the rest of the trip worth the money — even if you have to splurge a bit on hotels, restaurants, and other expenses.

Two of the most popular tools for searching for cheap flights are Google Flights and Skyscanner. And one reason why they’re so powerful is: both of these tools let you search for cheap flights anywhere, without having to choose a specific destination. If you’re flexible about where you are willing to visit, these tools can open up a world of possibilities.

Google Flights and Skyscanner also let you search by flexible dates. For example, I used Skyscanner to search for flights from my home city of Des Moines, Iowa to “Everywhere,” with flexible dates for the entire month of January 2024. Skyscanner quickly offered up a range of tantalizingly cheap flights to places I hadn’t imagined, like Puerto Rico for $164, and Jamaica for $289.

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Using Skyscanner in this way is a great chance to generate inspiration and ideas for your next winter travel experience. (“Would I like to go to Jamaica in January? Sure, why not! For $289, I can’t afford NOT to go to Jamaica!”) If you have flexible dates and if you’re open to exploring new places, you can quickly zero in on cheap flight deals and go from there.

2. Use travel deal services (some are worth paying for)

Another quick, easy, often free method to snap up winter travel deals is to use travel deal services. There are lots of these websites on the market, and many are free but some charge a fee for subscriptions.

One advantage of travel deal services is that they offer last minute deals. Sometimes airlines, hotels, and resorts will offer their best deals to people who book at the last minute, to keep that inventory from going to waste.

Here are a few websites that are worth checking for tempting deals on winter travel.

Going™ (formerly Scott’s Cheap Flights)

“Going” is hard to Google, but it’s a well-regarded travel deal service. This one lets you set up flight alerts: you go to, provide the name of your home airport, and then you’ll get emails with amazing deals on ultra-cheap flights — like 40%-90% off normal airfares. Some of the recent deals advertised on include:

  • Boston to Reykjavik for $100
  • New York to Barcelona for $282
  • Los Angeles to Athens for $460

Going™ has a free membership, but if you want to get even more deals with faster availability, you can sign up for a Premium membership for $49 per year, or Elite membership for $199 per year. Premium gives you access to hilariously cheap Mistake Fares (when airlines accidentally list flights for a ruinously cheap price, but still have to honor the mistaken fare), and Elite lets you see cheap flights in business class.

Dollar Flight Club

This is another cheap flight alert service. Dollar Flight Club sends you an email whenever a super-discounted flight deal (up to 90% off) pops up at your chosen airport. A few of the recent deals delivered by Dollar Flight Club include:

  • Greece for $320 roundtrip
  • Banff, Canada for $190 roundtrip
  • Costa Rica for $210 roundtrip

You can join Dollar Flight Club for free. It also offers a Premium membership for $69 per year (that unlocks additional deals, such as pricing mistakes and other shockingly cheap flights) and Premium Plus+ for $169 per year (dedicated to deals on business class flights).


I used to subscribe to Travelzoo back when it was a simple email newsletter. But now it’s a sophisticated website that you can browse to see an array of colorful, cheap vacation offerings; it’s like window-shopping for winter travel deals. Travelzoo membership used to be free, but from now on it costs $40 per year (starting from Jan. 1, 2024).

When I searched Travelzoo for last-minute winter travel deals, I quickly found several intriguing options, including:

  • Turkey: weeklong guided tours starting at $1,070
  • Cancún, Mexico: a four-night vacation at an all-inclusive resort, with airfare, starting at $1,139
  • Japan: 10-night trip, including airfare and hotels, starting at $2,999

Another benefit of travel deal services like Travelzoo is that its website quickly shows you a wide range of vacation packages, such as cruises, tours, or all-inclusive resorts. Sometimes it’s faster (and cheaper) to get great winter travel deals where the entire vacation is planned for you.

Bottom line: Want to find great winter travel deals? Start now. You can be proactive and search for your own cheap flights on Google Flights and Skyscanner. Or relax, grab your credit card, and let the deals come to you with travel search services and cheap airfare email alerts. Your next great vacation is waiting!

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