There are people who like dive bars and people willing to pay $100 for a few fancy cocktails. Neither option is right or wrong, it’s just a matter of taste. The important thing is that you’re happy with the price you pay and the service that you receive. Everyone can and should develop their own routines, rituals and priorities for finding the best travel plan for their specific needs.
While many people claim to have the ultimate ‘travel hacks’, the simple truth is that there is no one-size-fits-all solution out there. To be honest, it’s part of what keeps travelers going out on trips time and time again. If there were a way to truly optimize a vacation it would lose much of its adventurous charm.
In this article I’ll be breaking down my thought process when choosing flights as well as how to find great deals, whatever your budget may look like.
It all starts with a solid plan
In planning my travels I usually try to establish some clear goals and budget details ahead of time. If I know what I’m willing to spend before the trip even starts then I won’t have any tough decisions to make once the trip is underway. If I’m well within my allotted budget towards the end of the vacation then I may splurge on some fancier meals or get some exotic souvenirs.
Having a budget lets you enjoy your trip without feeling any remorse about overspending. The money was already earmarked to be spent on this trip, so spend the money in good conscience and enjoy your souvenirs. You don’t need to figure out exact costs of every single thing you’re planning to do; just ballpark the big expenses, round up and find a number that you’re comfortable with.
When building up a travel budget make sure to include the flights and factor that into your overall costs. If you’re looking to do some longer term travel take a look at my article on earning money while abroad to help bring down some of these bigger expenses.
Flight priorities trilema
Good, fast, cheap. According to conventional wisdom you can pick any two but you can’t have all three.
Generally this is true, although with a bit of luck and persistence you might find some surprising deals online. By setting up alerts on websites like google flights or kayak.com you can receive email notifications when flight prices dip down below the typical price range. If you happen to find an amazing deal it could be worth planning an entire vacation around. As I caution later in this article there are some other possibilities you should look into before racing to book that unbelievably cheap flight.
Unusual deals aside, I’ll pick the two most important of the three and make the best of the situation. Whether you sacrifice comfort, speed or savings is up to you.
I try to make sure my goals for the trip are aligned with the amount of time that I have off from work. If I’m on a tight schedule I’ll pay a little bit more to get to my destination ASAP. If I’m heading out for a 3 month adventure I might forgo some creature comforts to save a few hundred dollars. This might mean flying with a budget airline that doesn’t provide even basic in-flight services like drinks, snacks or checked luggage.
In most situations there is some sort of trade off, but if you’re consistently looking for flights you can scout some amazing deals. I still remember flying from Detroit to Paris one year for around $150… rest in peace, WOW Air… I guess those low prices really weren’t sustainable.
With this chart in mind, pick a flight that meets your needs for the specific trip. There is no correct or incorrect choice, so pick a flight that seems reasonable and get started planning your trip.
Research destinations to figure out why flights are so cheap
This is an extra step that can potentially save you from having a terrible trip on your precious few days of vacation time. You’ve done all of the right things, found an inexpensive flight to an affordable destination and you’re about to pull the trigger. This is a great time to make sure you fully understand why flights are so cheap this time of year.
A few relevant questions about where you’re traveling to could be: Is there a monsoon season? Is it too hot to go outside during the day? Is it too cold for tourism? Can you afford lodging when you get there? Is there a local religious holiday during the time you’ll be there?
I have friends who thought they were getting an amazing deal on a flight to Morocco but arrived right in the middle of Ramadan. Eating or smoking in public during the day is sure to elicit some scowls from hangry locals who have to fast while the sun is up. To avoid these types of situations, just make sure to do a little research before you book that suspiciously cheap flight to an exotic destination.
Incognito mode
Even though it’s not totally clear that this still works these days, it’s easy enough to do that I do it just in case. The idea behind this is that by using incognito mode your browser’s ‘cookies’ won’t be tracked by the airlines whose flights you’re interested in. Way back in the day they would use this information to charge more for flights you are repeatedly monitoring. While airlines may or may not be doing this anymore, it’s simple enough to open a new private tab so I do it just in case.
Building your trip around extended layovers
If there are multiple flights available at roughly the same price, compare a couple of options and see if any layovers sound interesting to you. If it’s through a city you’re interested in visiting and you have 2 weeks of vacation you might consider spending 3 or 4 days there before continuing on to the final destination.
Using tools like googleflights or momondo.com this has become significantly easier than it used to be. In this screenshot from momondo I’m looking at some possible options for a flight to Melbourne. Rather than taking an excessively long flight you could break it up using a multi-city flight plan.
This type of trip lets you customize your flight path to spend the time you want in cities that have connecting flights. Many times by opening another tab and looking at some dates surrounding your first choices you can find potential savings. While this option might take some more work you can end up spending a few extra nights in an inbetween city but saving money on your total flight package.
On some websites you can even sort by which airports you want to stop at on your layovers, allowing you to compare flight itineraries and decide what kind of loop would make sense for your vacation.
While this is a great option if you’re traveling light, it can start to get hectic if you’ve packed a few too many suitcases.
Packing as light as possible
I almost always bring just a backpack rather than checking a suitcase. Unless I’m moving to a new city or doing a sport requiring checked luggage it’s just not worth the hassle. Only bringing a carry-on means no lost luggage, no waiting at carousels after a flight and not worrying about your things getting smashed by TSA.
By minimizing the things you have to carry you can spend more time looking around and interacting with the country you traveled so far to see. Trust me, when you’re hauling your luggage up 3 flights of stairs and worrying about your belongings instead of relaxing it will already be too late.
Not only does packing light make it easier to move unhindered in a foreign country, it also opens up more possibilities. If you are dragging luggage around you limit your transportation options as well as flexibility when it comes to making spontaneous changes to your itinerary.
It’s tempting to be prepared for every eventuality but remember that there will be stores wherever you’re going. You can buy the things you forgot and you’ll have a souvenir that reminds you of the trip for years to come.
Parting thoughts
These were just a few points to get you started thinking through what trip design priorities you might include in your own routine. If I can stop just one person from ruining a trip by bringing too much stuff I’ll consider my job here done. There are also those people who will never go to a different country without checked luggage and that’s perfectly fine too.
At the very least I hope this article gets you thinking about how you want to book your next trip and save you some money in the process.
What does your trip planning routine look like? Drop a comment down below with your travel priorities and favorite websites or resources for planning trips.
Common resources for finding deals on flights and accommodations
Google flights
Integrated into the google suite which simplifies adding the plans to your calendar. I like that they compare prices across the year to tell you if you’re looking at a good deal or not.
Momondo.com
Another travel deal agregator that shows you deals and then redirects you to book directly with the airlines or hotels. Easy to use search function and interface.
Kayak.com
One of the more famous flight agregator platforms. Beyond flights they also have good searches for deals on lodging and car rentals.
Skyscanner.com
Good resource for booking multi-city trips and scouting good deals. They give well organized lists of cheapest flights out of your local airport starting with the least expensive.
Expedia.com
Acquired the travel site Rome2Rio and merged the two websites. Good for searching different ways of getting to a destination and comparing those costs
Airfarewatchdog.com
I particularly like the way they organize their flights with titles like ‘hiking getaways’ or ‘music scenes’. A useful tool for brainstorming and figuring out costs


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