How to Pick a Cheap Travel Destination

When I’m looking to book my next adventure, I usually start by figuring out a cheap travel destination for when I want to travel. It can be domestic or it can be international. Sometimes I have a place in mind and sometimes I’m ready to go anywhere that has cheap airfare. Yes, I’m that friend that’s always up for an adventure.

That’s how I ended up in Finland last year around this time for my family’s Spring Break. None of us had a burning desire to go see Finland, especially in early Spring when it can still feel like winter. But we were looking for an international adventure that wouldn’t cost a fortune.

When I was researching, I found a great deal and said to my family, “what about going to Finland?” They barely thought about it before saying, “sure, why not?” I’d say my family is generally pretty agreeable but they also trust me with our travel plans. In fact, I enjoy the planning process and if you do too, I’m going to let you in on some of my secrets for how to pick a cheap travel destination.

Know your seasons and markets

You may not pay much attention to high season (peak), low season (sometimes called off season), or shoulder season which is generally the period between the two. The benefits to traveling off season are much lower rates and typically lower crowds. But there’s usually a reason it’s off season and, most likely, it’s due to weather.

(Check out our off-season visit to Woodloch, an all-inclusive family resort in the Pocono Mountains!)

You might get a great deal on a cruise in August but just know that’s typically the most active time of hurricane season in the Caribbean. Personally, we’ve taken that risk before because ships are generally able to “steer around” hurricanes and alter port destinations if needed.

If you’re the parent of a school aged child, you’ll also know that travel tends to be most expensive when it happens to be most convenient for you, namely, winter break, spring break, and summer.

Europe is going to be expensive in summer. That’s just a fact. That’s why we try to squeeze it into our spring break when the weather is riskier but the fares are lower.

There are always exceptions to every season so definitely keep your eyes peeled if you want to head to a popular destination at the same time everyone else does!

If you do happen to see a good deal on a trip that falls during peak season, don’t be afraid to jump on it. But you might want to consider buying travel insurance in case your plans change. Also, make sure you continuing monitoring airfare because if your flight prices go down, the airline will refund the difference – but only if you ask them!

Pick your dates before your destination

If your heart isn’t set on a specific destination, keep yourself open with some low airfare tools. My absolute favorite for this is Skyscanner, which is both a free app and a website. Plug in your dates and your desired departure airport (I also check the box to Add Nearby Airports) and select “Explore Everywhere.” Your results may look something like this:

While the UK in August might seem like a fun idea, the rates might be much higher (or lower!) than you expected and it will save you from getting your heart set on a destination that isn’t feasible for you.

If you’re even more adventurous or flexible, you don’t have to pick a date at all. Simply select “Explore Everywhere” when you log in and you may find fares so low that you’ll start planning an unexpected weekend getaway (or change your vacation dates).

It must know me well because Japan is definitely on our bucket list!

Another quick tip – if you’re a Southwest flyer, like we are, you can also check the Southwest low fare calendar for a destination if you’re flexible on your dates. Sometimes flying on a Tuesday instead of a Wednesday can save you lots of money! (also – free bags on Southwest!)

Be on standby for those super low fare deals

Skyscanner is great for figuring out generally pricing for when and where you want to travel. But if you’re like me and know you want to go somewhere over Spring Break but you have no idea where (nor do you have the time to monitor fare sales), it’s totally worth it to sign up for a service like Going (formerly Scott’s Cheap Flights).

For $49 per year, I participate in a Premium Membership that gets me alerts on any great airfare deal out there from my home airports. Notice I used the plural…airports. I live closest to BWI (Baltimore) but I can drive to DCA (Reagan National) and IAD (Washington Dulles) easily. BUT, I’m only about two hours away from PHL (Philadelphia) and a little over three hours away (or a short train ride) to EWR (Newark). So by keeping my options open at these larger international airports, I have more possibilities!

When I was keeping my eyes open for a spring break destination for 2023, I got an email similar to this (this may have been the actual email that prompted me!).

Upon clicking through, I had to find a destination that still had cheap flights left for this sale that fits our dates and that’s how we ended up in Helsinki, via Iceland!

It’s the same way we ended up going to Rome for our spring break in 2024. We had to fly through Istanbul, Turkey but in the end it was worth it!

Going is also great at bringing you “mistake fares” which is when a very low fare is added to the market, often accidentally. If you can grab one of those and the airlines will honor it, you could get a ticket to South America for as low as $20 (seriously – I saw this mistake fare once many years ago when I was working in the travel industry).

And it’s not just for international flights. If you prefer to fly domestically, you can find fare deals for that as well. The $49 has more than paid for itself!

Save up points!

I am absolutely no points guru. There are people whose entire careers are spent figuring out how to play the credit card game and fly for peanuts. I aspire to be one of those people but I just don’t have the time to invest in that. If you do have the time and interest, you should definitely check out both The Points Guy and 10x Travel.

In the meantime, if you’re someone that uses credit cards regularly (primarily for new purchases, not for racking up a ton of debt!), pick a credit card or two that can work in your favor.

We fly Southwest Airlines a lot so my husband and I both use these cards. With the right deals and purchases, one of us usually qualifies for a companion pass. That means my husband books a ticket and I get to fly free with him. For our family of three, that means that when we fly Southwest, we’re paying for two tickets but flying with three! And honestly, on our most recent trip, our two tickets were booked with points and mine was free. Free flying – yes please!

My husband also travels a fair amount for work and tends to stay at Marriott properties. So it made sense for him to get a Marriott Bonvoy credit card. We get points for using it regularly and extra points when we use it to pay for a stay. Since he uses it mainly for business travel, his company reimburses him for the hotel stay and we get the points! We’ve used our Marriott points for a free night at The Industrialist – an Autograph collection hotel in Pittsburgh. We were able to use four nights at the Springhill Suites in Island Park, Idaho just outside of Yellowstone National Park. But the real kicker was spending an entire week at Hotel Katajanokka – a converted prison in the heart of Helsinki, Finland – for free!

Be ready to go at a moment’s notice

My final piece of advice is to stay open and stay flexible. Back in the day, I worked in the travel industry and got amazing deals just for travel agents. I went to Europe twice for $50 roundtrip (thank you, TWA! #rip). I spent four days at a brand new all inclusive resort in Mexico for $137 (flights included!). But I’m still kicking myself for not taking advantage of a one week trip to the Amazon (including flights) for $700. To be honest, I’m still not at a point in my life where I can drop everything and go when a deal comes up. But I’m getting there and I’m excited to see as much as I can without having a huge cash reserve.

If you’re the kind of person that requires a planned out, mapped out, fully catered itinerary, you’re probably going to pay for it. But if you’re open to new adventures and want to do it on the cheap, there are ways! My next step is working on finding more travel companions that want to go with me!