Surprise Savings: The Best-Kept Secrets of Cheap Winter Travel

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Want to score great deals on cheap winter travel? Keep reading to learn how being flexible can help. 

Want to take a cheap winter vacation? It’s never too late to find good deals, especially if you can be flexible on travel dates and don’t have a specific destination in mind. There are lots of good options to book cheap winter travel to help you get away for a few days (or weeks)!

A spirit of openness to new inspiration is what cheap winter travel is all about. Sometimes last-minute trips on a limited budget turn out to be the most fun, rewarding, and memorable travel experiences, especially if you use travel credit cards to save extra money and earn points.

Let’s look at a few ideas for how you can book surprisingly affordable winter travel.

1. Try all the travel search tools

Even though the cost of plane tickets has increased in the past few years, we’re still living in the Golden Age of cheap travel search tools. There are great websites you can use to search for affordable flights before you reach for your credit card to book a ticket. Here are two that we recommend.

Google Flights: I always start my airfare searches with Google Flights because it has easy-to-use search features for flexible travel dates and multiple cities. There’s a clear price grid where you can see how your airfare gets cheaper (or pricier) depending on the departure and arrival dates you choose.

Skyscanner: This is another popular search site for airfares and hotels. It has a powerful search engine that can combine multiple airlines and offer a wide range of possible itineraries. Skyscanner also has a new AI-powered “Discover with AI” search tool that lets you brainstorm ideas for cheap winter travel with just a few keywords about the kind of trip you want, like “Birthday trip” or “Cheap European city breaks.”

Both of these search tools let you search for cheap flights to anywhere in the world. This is a great way to quickly find surprisingly cheap winter travel and explore new destinations.

2. Be open to flexible dates, multiple airports, and different cities

Along with being willing to choose “Anywhere” as your destination, a key to finding cheap winter travel is being flexible about dates, airports, and cities. You might get cheaper deals by changing your departure or arrival dates by a few days, or choosing to fly on a holiday. My family once had an affordable winter vacation in Germany because we agreed to fly home on New Year’s Eve. If you’re not particularly sentimental about being on a plane during a busy holiday, you can often score cheaper flights.

You also might be able to get cheaper airfares by searching at multiple airports, even within the same city. When you search flights, make sure you search for a destination city, not just a destination airport. For example, if you want to fly to London, choose “London” the city as your destination, not just “London Heathrow Airport.” You might get better deals by flying into a smaller airport in a major city.

Or depending on where you live, you can often find cheaper airfares if you’re willing to drive to a different city’s airport. My family lives in Iowa, but we’ve taken several international family vacations by flying out of Chicago O’Hare and Minneapolis. Sometimes we saved over $1,000 on airfare by being willing to drive for a few hours. Think about your total vacation budget and how much time you’re willing to spend on the road.

3. Don’t be afraid to combine airlines

Some of the cheapest flights can often be found by combining your trip across multiple airlines, including some budget airlines. You might end up with a wacky-looking itinerary where you have to transfer between airlines. But if the airline tickets are significantly cheaper, this can be worth the hassle — especially if you’re traveling light, with only a carry-on bag and don’t need to worry about your luggage getting lost.

What if you could save hundreds of dollars by switching airlines? Isn’t that worth a little extra hustle during an airport layover? I recently searched on Skyscanner for flights from my home city (Des Moines, Iowa) to London on Jan. 4 to Jan. 10, 2024. The typical price for flights on a single airline was $1,188 roundtrip. But by combining airlines (and accepting a longer trip duration with multiple airport connections), I found a flight for only $779 — a savings of $409.

4. Embrace a long layover (or stopover)

In that same spirit of flexibility, keep in mind that if you want cheap winter travel, a long layover doesn’t have to be a bad thing. Sometimes you can find the cheapest flights if you’re willing to hang out at the airport for a few hours, or even stay overnight in a different city along the way.

Depending on your travel plans, these long layovers and overnight stopovers can be fun! What if you have a 12-hour layover in a big city you’ve wanted to visit? Leave your bags at an airport locker and take a little day trip. An overnight stopover can also give you a chance to explore a new place.

My family once got to have a wonderful European vacation because we agreed to an unusual flight connection that had us stay overnight in Madrid, Spain, on the way home. But we loved it! It was a fun chance to see Madrid, we stayed in a cute Airbnb, and we got to eat Madrid’s famous tortilla española (potato omelet) for breakfast.

Bottom line: Even during times of rising airfares, cheap winter travel is totally doable. Just go into it with a sense of openness. You might need to accept a longer flight itinerary, connect through multiple airports, switch airlines, or stay overnight in a different city along the way. But good travel is all about curiosity. You can save money on flights and find joy in the journey!

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