Families, school faculty, academics, and anyone else tied to a school calendar know all too well that traveling can be stressful … and expensive. It's something we hear from travelers constantly.
Teachers want to take a vacation (which they badly need), but can't afford the insane fares to get themselves to the beach during the limited dates they're allowed to travel. Families want to vacation, but spring break flights are $1,000 a piece. When everyone has time off to travel, that demand sends prices sky high.
Here's the hard truth: The deck is stacked against travelers tied to the school calendar. But it isn't impossible. We have several members of the Thrifty Traveler team who do it all the time. So I asked for their help and the help of many of our readers and subscribers who offered their best advice to book travel around school.
The key is booking early, staying on top of your booked flights and hotels, and using whatever flexibility you have to your advantage.
You can be a student, teacher, administrator, staff member, or parent and still see the world. Here's how to get it done!
Book Way, Way Far in Advance
When it comes to booking airfare, it pays to be proactive … and I'm talking about up to a full year in advance, proactive.
If you're tied to a very specific schedule and everyone else in your area is on the same schedule, you have two options: Go set the market for airfare, or react to what others have set for you. Let me explain.
You know your school schedule years in advance – but the airlines don't. The only way the airlines get that kind of information is through booking data. That's why, during the week of spring break, you might see airfare that is four-or-five times higher than the week before or after. It's because travelers have been gobbling up those seats and setting a new demand environment. (The airlines aren't reading your emails or listening to you through your Alexa. You are just late to the party and other travelers have set the demand environment before you got there.)
So here's what you should do: Get there first! When flights first go on sale (which is almost always 11 months before travel), you should be the one to gobble up the first couple of seats and set the price for everyone else.
Thrifty Traveler Co-Founder Nick Serati and his family of five love to go somewhere for spring break, which, as you can imagine, can get tricky.
“The biggest thing for us is planning ahead and knowing the schedule before the airlines do. For example, the calendar opens for our spring break 2026 dates this coming Saturday so I am planning to book something. I have been keeping an eye on the flights that are available so I have a pretty good idea of what I am going to do come Saturday … and then rebook if the price drops. Though that likely won't happen (at least not in my experience),” he said.
The key to Nick's strategy, besides being first, is to book a flexible fare. If you lock yourself and your family into a basic economy ticket, you might get stuck with the full bill or at least a hefty change fee if your plans change. And everyone with kids will tell you that a lot can change in 11 months!
You can do this by booking Main Cabin fares and above. That will allow you free changes and cancelation for a voucher. But the absolute best way to do this is using points and miles. When you do that, you're taking on even less risk, because you don't have all that cash tied up with the airline, and most airlines will just redeposit your points in your account if you need to cancel.
Finally, it might make more sense to book one-way flights instead of the traditional roundtrip. Canceling or changing an itinerary is much easier if you booked one-ways. That way, if you find something better or different on one segment, you don't have to cancel the whole thing to make changes. If the flights are the same cost one-way versus roundtrip, always book the one-ways.
Be first and book flexibly. That's how to ensure you get the best price and make your vacation a reality.
Or at the Last Minute…
If you didn't get your flight booked 9-11 months ahead of time, you're next best opportunity might not come around again until about 3-8 weeks before travel. It might be an agonizing eight months watching fares go up and up and up, but sometimes, there's some relief right at the last-minute, too.
Airlines often slash prices to destinations that aren't selling well enough. Think of it as the clearance rack of travel deals.
Check out this example of flights from Denver (DEN) to Calgary (YYC) near Banff National Park. While these summer break fares were closer to $400 roundtrip over the last few months, now that we're under eight weeks away, fares have dropped precipitously because bookings aren't as strong as the airlines hoped.
The same goes for points and miles award availability, too. It depends on the airline, but with Star Alliance airlines like Lufthansa, SWISS, and United, some bonus award availability typically comes online about two or three weeks before travel if it hasn't sold by then. For example, I did a quick search through Air Canada Aeroplan to see if I could find a business class flight to Croatia later this April. Lo and behold…
It pays to look around and be flexible if this is your strategy. The example flight above, of course, has an overnight layover in Zurich (ZRH). (Which I'd happily take. I love Zurich!) But you might not get the cream of the crop itineraries in some cases.
Use Google Flights Explore
If you're dead set on going to Cabo, you're going to have to pay Cabo prices – whatever they are. But if Cabo prices don't fit into your budget, turn to Google Flights Explore. It's our single favorite flight booking tool. Here's what you do:
- Go to Google Flights
- Put in your desired departure city.
- Put in “Anywhere” or something broad like “United States” into the destination section.
- Put in the dates of your trip or school break.
- Add any other filters or requirements you have.
- See what's out there!
When you do those six things, you get a map full of flight options like this. For this search, I looked from Chicago (ORD) for Christmas break flights. As you can see, it's fairly expensive to get to lots of destinations that week … but then you see San Francisco (SFO)! Sub-$300 roundtrip flights to the Bay Area could be an awesome Christmas break trip. A little skiing in Lake Tahoe? Heading up to wine country? Maybe a trip down the Pacific Coast Highway to Carmel-by-the-Sea?
Even though you maybe didn't have SF on your list, you followed the cheap fare and booked an awesome trip that works for your dates thanks to Google Flights Explore.
Read Next: Our Full Guide to Google Flights Explore
What About Hotels and Lodging?
For that, we're going to turn back to Thrifty Traveler Product Manager Tracey Burtch, who's a wealth of knowledge on this topic. For her family, booking hotels – especially abroad – can be the trickiest part of travel.
That often means booking several different hotel stays using points, knowing that she very well might have to cancel, but resting assured that her family will at least have something to fall back on in the end.
“I can't tell you the number of times I book a hotel on points so that I'm holding it just in case the trip happens or those dates work out. Yes, it means having some points locked up with that hotel so those with fewer points or transferable points may need to give this more consideration,” she said.
And while it's not school schedule-related, she just booked a few hotel options for the 2026 Milan Olympics and once she knew the dates she could get tickets for, she just cancelled or adjusted it to match those dates. She uses the same strategy for booking Christmas break, Spring Break, and summer break trips, too.
There is something that many points and miles travelers often overlook when booking international hotels, Tracey says. It's something to be aware of when you're booking a trip around the school calendar.
“Many of the places we've been don't have rooms for four people – and the common thought or advice is to just book two rooms. We usually prefer not to do this so I sometimes focus on booking flights using points and use cash or travel portal credits for hotels. I'm calling our summer 2025 Europe trip a tour of Premier Inn – one of the few hotel chains that commonly offers rooms for 4 people. It's not at all luxurious, but it works for this type of trip!”
Of course, the best option of them all for most traveling families is to book a vacation rental. Sites like Airbnb and VRBO offer homes that are often already suited for traveling families. It allows you to spread out, have separate rooms, and will often come at an even better price point than hotel rooms. To get the best rate on your vacation rental, use this incredible trick to get a lower price, too.
Book Early, Book Often
As a so-called travel expert, I get asked for advice all the time. Here's the one piece of advice I swear by and tell every traveler in my life: Never stop booking your trip.
I'm not done booking a trip until I've unpacked my suitcase back home. I'm always tinkering with my travel. And it's saved me thousands and thousands of dollars over the years, as well as put me in comfier and comfier seats.
It's how I turned an economy ticket into business class flights to Europe in 2023. And it's how I did the same thing turning an economy ticket into the best business class flight of my life to Japan in 2024. Will I do it again in 2025? 100%.
One of the biggest mistakes I see travelers make is booking flights and then filing their confirmation emails away in their inboxes until the week they travel. Here's what I'd recommend you do instead.
- Book a flexible flight (Main Cabin and above) as early as you can.
- Set Google Flights Price Alerts to track the price so you can rebook the new, cheaper flight and save money if prices drop. (Set price alerts for alternatives to your flight and to alternative destinations, too!)
- Set a monthly (or more frequent if you have the time) reminder to spend 20 minutes and re-search all of your travel to see if you can find something better out there.
- Rebook and rebook and rebook to get the cheapest, comfiest seat or lodging option possible.
Another tip for more intermediate or advanced travelers: There's no rule against having multiple flights or hotel rooms booked at the same time for the same trip. Sometimes, I've had two or even three different flights booked for the same trip. (Usually on different airlines, most airlines won't let you have two itineraries between the same cities at the same time.) Then, as I get closer to my travel day – even within just a few days or hours – I can decide what flight is best for me and cancel the rest for a refund.
Don't book a trip and leave it in your inbox for 10 months. Set price alerts, keep checking for better options, and stay on the hunt for cheaper or better lodging too.
You should never be done booking a trip. Travelers that stay on top of their itineraries travel better and cheaper.
A Little Flexibility Goes A Long Way
All of the tips I offered above work for the traveler who is dead set on not missing any school. For some families, that's a non-negotiable – I get it. But if you are willing to miss a day here or a day there, adjusting by one or two days could save you thousands of dollars and big time travel headaches, too.
Here's the easiest way to frame this: The most expensive, busiest, and most stressful days to fly are Fridays and Sundays. The least expensive days to fly are Tuesdays, Wednesdays, and Saturdays. Monday and Thursday are typically somewhere in between.
The problem is, of course, that travelers tied to the school calendar want to leave Friday after class and get back Sunday before school begins the next morning. But everyone else on Earth also wants to fly at those times, making them the most expensive times, bar none.
Let me rant about Sunday for a second: Sunday is by far the worst day to travel in every measurable way. I think it's crazy that travelers always book Sunday flights and pay way more to do so. If you can avoid flying on Sunday, you're going to save hundreds and hundreds of dollars, and avoid the most stressful, tense day at the airport when everyone is desperate to get home, the airport is busiest, and everyone is facing the highest fares. Sundays at the airport are the absolute worst. Avoid them at all costs – especially with the full family in tow.
Saturdays at the airport are a delight, and are a great alternative if you want to shorten your trip by a little bit, but the better option is going to be flying home Monday or Tuesday. That allows you to enjoy your full weekend and then travel on a much less tense (and much less expensive) day. If that means missing a day of school, you'll have to determine what that's worth to you.
Don't slam your laptop shut after seeing high fares on a Friday-to-Sunday itinerary. Small adjustments can lead to massive savings.
Bottom Line
Travelers tied to the academic calendar have it harder than everyday travelers. But using a few key strategies, you can still travel inexpensively as a parent, student, or school staff member.
The advice we have here is simple: The key is booking early, staying on top of your flights and hotels, and using whatever flexibility you have to your advantage.
