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Penny Pinching Flight Search

Penny Pinching Flight Search

Are you looking for a way to go on vacation for cheap? This penny pinching flight search guide is for you!

We’ve heard it all:

“How do you travel so much?”

“You must have a lot of money”

“How do you afford all of this?”

Eye roll

Honestly, it gets kinda old after a while. Plus, I personally think its kind of rude! I mean, you wouldn’t ask someone

“wow how do you afford your house?” or

“How do you have enough money for your baby?”

“That’s a big TV how do you afford that?”

Amiright? It’s not that we don’t want to talk about it, because we certainly do! Traveling is one of our biggest passions, and of course, we want to share our knowledge. But, it often feels like a personal attack when we are asked these kinds of questions. 

So today we will share our answers to these types of questions:

“Can you help me find some good deals?”

“What suggestions do you have for someone looking to travel cheaply?”

Disclosure: Some of the links below are affiliate links, meaning, at no additional cost to you, I will earn a commission if you click through and make a purchase.

Secrets to cheap flights

Step 1: Pre-Planning

The first step to your penny pinching flight search is pre-planning. Any cheap vacation starts with some rigorous planning. Start by creating a list of 3-5 destinations you would feel excited and comfortable to visit.

Your list should include places you realistically might be able to afford, as well as some crazy or far-fetched ideas (because you never know!)

Next, take a look at your calendar. Do you have set times or weeks off? Long weekends ahead? How many days off can you take in a row from work?

Find 3-5 dates that work for you throughout the next year or so. Be realistic in the number of days you intend to take vacations, and factor in any pre-planned activities you already have planned. 

Take note of any neighboring airports during this step. You might want to look at flying out of different airports for cheaper results. Driving an extra hour or two to a different airport could save you hundreds! 

Take some time here to decide if you want to travel domestically or internationally. This will give you an idea if you need a passport or a visa.

Passports can take time to issue, so planning ahead can ensure you have everything you need before you travel. You might not know yet, but starting the passport process is highly recommended at this stage.

While you’re at it, get yourself a cute passport holder like this one!

Step 2: Stalking!

The second step for your penny pinching flight search is to stalk! 

In all seriousness, this is essentially what you will be doing for the next few months.

Spend ~1-3 months stalking all the airline websites. I rely heavily on Priceline, as I have found them to be the cheapest and most reliable source for booking flights. I have never had any problems booking with them, and they even have the name your own price tool, which can save you a lot of money!

Start by searching your desired locations during your designated travel dates.

It is helpful to be flexible with your dates: look 3 days earlier and 3 days later for the best results. If there is a monthly view calendar, that can be extremely helpful as well, to see trends of prices for different days. 

Take note of the average costs during this step. You might notice some locations are much cheaper than others, or some dates are double the cost of others.

Spend the next few months continuing this step. Search at different times of the day, different days of the week, and compare your prices.

Writing your results down will be helpful at this point. I have a travel journal I love to use at this step. This travel journal does a great job of helping you keep track of all your information!

Additionally, you will want to continually clear your website data and cache, or use an incognito window. This will help keep websites from tracking your searches and increasing your prices.

Soon, you will notice some patterns. You will notice prices to certain locations at specific times are always around the same cost.

This is good! This is what you want! You want to establish a cost baseline for yourself. 

Your cost baseline will give you a general idea of how much money you might be spending soon. The cost baseline will also help you determine what a good deal is in the future if the price changes.

If it is still too much money, go back to step 1 and look at different locations, or look into booking your trip at a further date to give yourself more time to save. 

Step 3: DO IT NOW

The last step for penny pinching flight search is to book! Here is where the adrenaline sets in.

You know your cost baseline, so you will know a deal when you see one.

I suggest considering the price a deal if the cost is at least $100 below your baseline. For example, last year while looking for tickets to Santorini, Greece, our cost baseline was upwards of a thousand dollars.

Without knowing this, we would not have known that the flight we got ($400) was a deal!

You need to know that what you’re looking at is, in fact, a deal.

And when you see that deal…


Don’t wait until tomorrow (it might be gone). Don’t think it over. Just book it. You’ve been planning for a while now. You know its a deal, you are prepared, don’t hesitate. 

You might be just getting into bed and you decide to do a quick search.  Then BAM. You find it! $200 off! That’s when you get your credit card out and book away my friends!

Now, get packing! If you haven’t already, get yourself a solid suitcase. I don’t like to check bags (for fear they might get lost), so I use this one, which is small enough to use as a carry on, while having enough space to hold all my stuff!


There you have it, fellow travelers. Hopefully, this penny pinching flight search guide will help you with all your budget travel needs. There are few tricks for cheap flights other than patience and doing your research

If you are looking for how to find cheap hotels, we have you covered!

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Monday 18th of May 2020

These are actually great ideas in concerning blogging.


Monday 18th of May 2020

Thank you ever so for you article post.


Monday 18th of May 2020

Like!! I blog quite often and I genuinely thank you for your information. The article has truly peaked my interest.


Monday 16th of March 2020

Hello, I was wondering what time of year/how far in advance you booked your flight to Greece for 400 dollars??? I have been dying to go, but the price is always so crazy, I would really appreciate your help!

Monday 16th of March 2020

Hi there!

We booked our flights on travel Tuesday which is the Tuesday after "Black Friday", so we kind of lucked out! We went in June which is a pretty popular time to go. Honestly I think we just got lucky, but we always find good deals on travel Tuesday!

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