How To Book The Cheapest Flights

Learn how to book the cheapest flights so you can save your money and explore more while you're there. Learn the industry's top tricks and save today!

Traveling is so exciting once all of the planning is finally done. The costs can quickly add up in the process, leaving you with little to spend while you’re actually there exploring! Unlike rental cars or museums that have generally consistent costs, flights are a huge way to save if you navigate it well and do the research. This article will help you book the cheapest flights so you can save where you can, and explore more!

Check out the following resources to help you surf the web and find the best deals for you!

View out of a plane

Table of Contents

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Summary

1. Check your Points

2. Discount Flights

3. Flight Search Engines

4. Airline Direct

5. Check again within 24 hours

Be ready to take these offers with the flexibility of destination and date, pack light to save on luggage costs, and travel in the shoulder seasons!

Flight Search Engine

Myth or Fact?

1. Flights are Cheaper on Tuesdays

Myth. However, it is in fact cheaper to fly on a Tuesday, as well as on Wednesday and Saturday. The day of the week a flight is booked is irrelevant, however, there is a difference in flight cost depending on the length of time until the scheduled flight! It’s typically best to book early (2-3 months), however, there are some unbeatable last-minute flight deals!

2. Search in Incognito Mode

Myth. While flight prices do fluctuate on the market and demand for a particular flight, your search patterns will not influence this! Flight prices are constantly changing, but your cookies have nothing to do with it! However, if you don’t search in incognito mode, be prepared for endless ads!!

3. Flying a Budget Flight is Always Less Enjoyable

Myth. While there definitely are a lot of cheap flights out there that have some pretty significant drawbacks, there are some gems you can find for a good price. Often, flights are reduced in price due to a long layover, a self-transfer between airports, limited baggage, and a lower-quality experience. Check below for the discounted flight sites where you can find insane deals without all of the extra negatives!

Before You Start

Be Flexible

The key to cheap flights is flexibility. You may find flights that have crazy long layovers in another city or better options on a different day. Maybe, you aren’t super attached to any specific destination, so you can be flexible there too!

Another big consideration is your luggage – many budget airlines have baggage limitations. Keep your options open and ready to grab by traveling light and being flexible. 

The more flexible your plans are, the more options you can take advantage of!

Start With What You Know

Start with what you know and search from there – there are a lot of variables to consider and some may be necessary for you to keep consistent. For example, you want to go to South America but don’t care when or which specific country. Or, maybe you have 2 weeks off in the spring and want to go anywhere during those dates. These are 2 completely different situations that require different approaches

 

So, do you know the dates you want to travel? Do you know where you want to go? The cheapest flights can be purchased with the most flexible plans! Do yourself a favor and see if you can get a bit of wiggle room with both the destination and the dates. 

The 24-hour Rule

Once your flight is booked, you have 24 hours to cancel (this is a federal law in the US). Since flight prices fluctuate daily, you may find that the flight you purchased went down in price just hours later! If you’re a real bargain hunter, go ahead and cancel your flight to purchase the better option. 

This is also a good thing to know when you come across a good deal. Found a flight you can’t pass up? Book now and sort out the rest after, you never know how long the prices will last!

Let’s Go Through an Example of the Process:

1 Passenger with 0 bags traveling from San Francisco (SFO) to Costa Rica on October 18, 2023. The dates are slightly flexible +/- 7 days, and the airport in Costa Rica does not matter.  

*These figures are researched on August 29, 2023 – <2 months before the trip. 

Step 1. Fly Free With Points

For any budget traveler, getting the right credit card and cashing in on those points is essential. Not only will they help cover travel costs if things don’t go to plan, but with the right card you can accrue points that you can cash in for flights!

Especially if you’re not a frequent flyer, you’ll want to use those points whenever you can, so start here! Check your credit card’s points value, and see how much that translates to in-flight miles. Typically the points can only be used when the flight is purchased through the credit card’s website, and these aren’t typically the cheapest options. So that’s up to you to decide if the points are worth using this time around. 

Find the best deal you can with your credit card points, and then continue to Step 1 and beyond to see what you’re comparing it to! You may find an awesome deal within the steps below that makes you want to save your points for something else. 

Chase Sapphire Preferred

This is the best travel card for its travel benefits. Earn 5x points booked on travel through Chase, earn 60,000 points when you spend $4,000 in the first 3 months, get comprehensive travel insurance, and more!

Example: Chase Sapphire Preferred

I use the Chase Sapphire Preferred Credit Card – Through the Chase app, I found a flight for $205 on October 17 – a great option to compare to after the final steps!

By booking through Chase, I can use my Rewards points to pay for the flight, making it essentially free!

Step 2. Discount Flight Sites

You have probably heard of these discount flight websites – they offer insanely low prices for select flights. This is a great place to start, especially if your plans are flexible. Let’s break down some of the most popular discount flight sites!

Going through 3rd party groups can create a complicated customer service network. Be sure all info is accurate before booking to avoid unnecessary headaches!

Going (formerly "Scott's Cheap Flights")

Going is a subscription-based search engine connecting you with discounted flight deals departing from your home airport. You choose the destination, and Going will provide alerts of insane deals that can get you there for cheaper.

Subscription tiers are either Limited ($0/year), Premium ($49/year), or Elite ($199/year), each offering increased benefits to get the best deals. The deals are found by a team of people who search for the best options. However, there are limited features showing only round-trip tickets!

Example: Going

In Going, I found 1 deal that matches a flight from SFO > Costa Rica. A round-trip Avianca flight for $350 in September-November, with more options available by changing the date!

*This is round-trip, however, the link directed me to Google Flights where the price was $150

Travel Pirates

Travel Pirates uses a tried and trusted search engine to guarantee quality flight options – KAYAK. However, what distinguished Travel Pirates from KAYAK, is not the search feature, but the deals lists. Travel Pirates uses a team of deal hunters to put together the best deals for flight, transport, and accommodation while considering the overall value of the option (for your money & time)!

Example: Travel Pirates

In Travel Pirates, using the ‘Plan Your Own Trip’ feature, I found a flight for $135 on October 18! Within the deals section, there was a discount for $133 across LATAM – with further inspection, the $135 flight found through the specific search was the best option!

The Dollar Flight Club

The Dollar Flight Club works similarly to Going – where you input your home airport, ideal destinations, and date range and the platform will provide alerts when there is a low price. There is a free option, with the upgraded subscription available for $ /year. 

One major drawback is you cannot specify whether it is a one-way or round trip, providing skewed results. The results direct you back to either Skyscanner or Google Flights to further investigate. So if you know where you want to go, just go straight to Skyscanner / Google Flights and skip this step, however this is a great place to take advantage of deals found for random destinations around the world!

Example:

In The Dollar Flight Club, I found the applicable flight through Avianca listed online for $135, however, with further inspection the price was actually $150 as I was directed to Skyscanner and Google Flights. 

Step 3. Flight Search Engines

If you didn’t find any killer deals from step 1, then we move to a broader search with these flight search engines. These are technically an Online Travel Agency (OTA), which have their own added fees and discounts applicable. So, even if all of the search engines you use pull up the same flight options, you may see different prices! That’s why it is best to use them all and compare!

 

Protect your flight costs with the best Travel Insurance.

Google Flights

Google Flights is many travelers’ starting point when looking for flights. This is a user-friendly platform that provides a great baseline for what to expect in regard to price. Google Flights considers both major & budget airlines, offering a wide range of options! It also has some helpful features including: 

  • ‘Explore Everywhere’ feature
  •  Low price alert
  • Calendar price view to show cheaper dates
  • Extensive filters

Example: Google Flights

Using Google Flights, I found the same $150 flight with Avianca that many of the Discount Flights found. However, it also showed that if I changed the date from Oct. 18 to Oct. 20, the price would go down to $81

Since that’s only 2 days and a very reasonable flight schedule, that is the best option so far!

Google Flights is the best place to start to find the cheapest flights
See the "Travel on October 20 for $81" pop-up!

Skyscanner

While no flight-searching platform is consistently the cheapest, Skyscanner would definitely be a top contender. This platform is reliable and has a well-supportive customer service department. 

  • Often has the best prices!
  • Explore Everywhere Feature
  •  Low Price Alert

Example: Skyscanner

Using Skyscanner, the best flight is $150 through Avianca. This is the same search result as the Dollar Flight Club above!

ITA Matrix

Owned by Google, the ITA Matrix is a common tool amongst travelers, that compares the prices of major airlines. This is another great way to get a baseline, but it often doesn’t boast the best prices. ITA Matrix has a unique UX compared to many of the other sites, which, is preferred by many users due to its expansive filter options. 

  • Low price alert
  • Calendar Price View
  • Does not include budget airlines
  • You must use the exact destination airport code

Example: ITA Matrix

Considering the ideal date of October 18, ITA Matrix provided a JetBlue flight option for $205. However, their calendar view showed a cheaper option for only $81 on October 20. 

Since 2 days is worth a $124 savings, the $86 flight with Frontier is a better option. 

Momondo

Momondo is a part of the Booking Holdings Corporation, which owns KAYAK, Expedia, Booking.com, and more. However, this site has a fun style and quality options! One of the best features is the Flight Insights view to see historical changes and the best times to go!
  • ‘Search Anywhere’ feature
  • Low price alerts

Example: Momondo

Using Momondo, the cheapest flight on October 18 is $150 with Avianca, as reported above by other sources.

Kayak

If you open KAYAK after Momondo, you’ll notice they are extremely similar, and so far I can’t see any difference! 

  • Flight price alerts
  • ‘Explore Everywhere’ feature
  • Date Range filter

Example: KAYAK

KAYAK shows a $150 flight from Avianca 

Step 3. Straight To The Source

Once you find the best flight at the lowest price, you may want to check out and be done. However, it’s worth it to go straight to the airline site and see if they offer the flight any cheaper. Sometimes, they even have discounts and deals on their website to encourage you to purchase through them rather than a 3rd party agency. Call customer service and see if you can lock in anything cheaper!

Example Decision: San Francisco to Costa Rica

So far, the cheapest flight from San Francisco > Costa Rica is $81 from Frontier as seen on Google Flights & the ITA Matrix. 

However, this flight is for October 13 or October 20, and if flying on a Friday doesn’t work, then the best option is $150 through Avianca on the 18th. 

Let’s move forward with Frontier!

The website does have a discount offer for members of the ‘Den’, however, this is a membership service costing $60/year and $40 enrollment. Definitely not worth buying into that unless you fly Frontier often!

So with some time and research, you found a flight for only $81 to Costa Rica using Google Flights.. time to pack your bags and get to planning!

Now that your flight is booked, get ready with everything you need to know about an International Phone Plan!

Summary - How To Book The Cheapest Flights

There are dozens if not hundreds of flight-searching options out there. You could spend your life finding deals and saving the most, but your time should also be valued in this process! 

The more flexibility you can have in your travel plans, the easier it is to find flight prices you feel good about. Some major ways to save include traveling with only a carry-on, traveling mid-week, and going during the shoulder seasons.

There is no perfect answer when it comes to finding the best flight, so start with some ideas about what you want to prioritize so your primary needs are met, and the rest will fall into place!

Posted by Taylor Mallaber

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