My Secrets for Booking Cheap Flights

I’ve discovered there are 2 types of people when it comes to travel and money. You are either the type to travel often and cheaply, or you are the type to go once a year and go all out!

If you have been hanging out here for a while, you know that I write for the folks who want to travel as cheap as possible and as often as possible. Sorry to the others, you won’t find super glamorous and fancy trips on here! Might I suggest, Conde Nast Traveler? 🙂 

When it comes to travel, I am all in on knowing what is and isn’t worth spending a little extra cash on. Obviously, this is totally subjective to the traveler. For me personally, I prefer to skip priority boarding and fancy hotel rooms in order to make more room in the trip budget for excursions. 

That being said, over the years, I have picked up a few tips and tricks in the cheap flights department. 

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Flexibility is Key

The first and biggest tip I can give you is to remain flexible. With, like, everything. Here’s my disclaimer: I am self-employed. I understand my hours are more flexible than average. However, I really do think everyone can apply this tip. If you can’t choose your dates, try to be flexible with the destination. If you are set on a certain destination, try and plan far enough in advance so that you can ask off and go during the week! 

Download SkyScanner 

I’ll wait. Downloaded? Okay cool. Now we can talk. This app is my game changer. Now, are all flight booking apps about the same, price wise? Honestly, probably. However, SkyScanner’s explore function is what sets it apart from the others. Through its explore tab you can set your home airport and view flights to anywhere leaving anytime. Remember how I said you have to be flexible?? Yeah, this is where that comes in. 

Many of my past trips happened because I (or a friend) found irresistibly cheap tickets on the explore tab. I wasn’t planning on going to Banff or looking for flights to Iceland. We just found them and booked them. During this season of my life, it really is as easy as that. 

SkyScanner also works for specific dates/destinations and I have often used it for that. Obviously, not all of my trips are off the cuff. Often times, I have to be in a certain city on a certain date. I check SkyScanner before booking these as well. Just enter your dates and the airport codes and it will scan airlines for you and get you the cheapest! 

Tip: Southwest *usually* isn’t listed on these sites. If I am booking flights for a planned trip, I always run my dates through SkyScanner and Southwest separately. 

Airline Credit Cards 

All my friends know how much I love my Southwest cards. Yes, cards. Plural. Because I have 2 of them. I have to make another disclaimer: if you cannot pay off your credit card in full every month, it won’t save you any money. Free flights aren’t free if you are paying interest. Okay, now that that is out of the way, let’s talk about airline points, friends. 

Almost always, airlines will offer you a huge point bonus for signing up for their card, once you spend a certain amount of money within the first couple months. A common promotion for Southwest is 40,000 bonus points when you spend $1,000 in the first 3 months. If you are looking into a card and you don’t see a promo, depending on your situation, it is probably worth it to wait. 

When it comes to choosing which card you want to apply for (and just life in general), a little bit of math goes a long way. Look into what having that card entails. Annual fees? Anniversary bonus? Companion pass? Bonus points on groceries? Look up how much one point is worth for that airline and then do some good ole fashion multiplication, division, addition, and subtraction and crunch the numbers on each card you are looking at. Then choose the one that best suits you. 

For reference, the 2 cards I use are the Southwest Premier Business card and the Southwest Priority card. I also have a Delta card that I use for international flights. 

Quick Booking Tips 

As someone who is constantly searching for flights, I have learned a couple quick things that can make a difference on flight prices. 

For Southwest: Tuesdays, Wednesdays, and Thursdays are typically the cheapest days to fly. Look at the first and last non-stop flights of the day; I usually have luck with them. 

If you are going international, it might pay to get crafty with your flight bookings. When my mom and I went to Europe we saved thousands by booking a flight from Venice to New York and then New York to St. Louis, rather than Venice straight to St. Louis. Yes. Literally thousands. 

If you can, weekday flights in the early morning or late evenings will usually be cheaper than a flight at prime time. 

I do not have experience to back this, but I have heard that you should always book on a Tuesday and never book on a Sunday. 

I think that wraps it up for today, folks. If you are a cheap flight enthusiast yourself, please brag on your best flight find in the comments! I would love to hear about it! 🙂 

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