The Ultimate Guide to Booking Flights

There are only two ways to book a flight online – directly with an airline or through an online travel agency (OTA). Yet, with countless considerations – price, airline rating, flight duration, frequent flyer programs, and available seating, to name just a few – the flight booking process can feel overwhelming.

This ultimate guide to booking flights will provide you with a simple framework for navigating all these considerations effortlessly so that you can be sure you’ve found the perfect flight every time.

The first step to booking a flight is to learn what flight options exist. To keep things simple, let’s assume that you know the approximate dates you plan to travel and your destination.

Flight search engines, such as Google Flights and others mentioned below, collect flight data from hundreds of airlines and allow users to sort flights based on their preferences. This makes them the ideal place to start.

In most cases, the top flight search engines offer the same flight data and have similar features, so it’s more about which interface you prefer. It is worth noting that flight search engines do not sell tickets directly, but will instead redirect you to the airline or an online travel agency for booking.

Google Flights

Our starting point when booking a new trip is Google Flights. It provides flight data for almost every global airline in a format that makes finding the best flight options effortless. Once you enter your departure and arrival locations, ticket type (i.e., economy, premium, business, or first class), and travel dates, Google Flights will display all your flight options and then allow you to filter by the following preferences:

• Airline or airline alliance
• Number of layovers
• Price range
• Departure/arrival time
• Connecting airports
• Total flight or layover time
• Bag fees
• Emissions amount

If your travel dates are flexible, Google Flights offers several additional features to help you get the best pricing:

• Date Grid – shows how your flight price changes if you change the departing and/or return travel date(s)
• Price Graph – shows how your flight price changes if you change your departure date but keep your trip duration the same length
• Price Insights – shows if your flight price is low, normal, or high compared to the trailing 90-day average of the same flight

By using a combination of Google Flight’s filters and features, you should be able to determine what your preferred flight options are. If you select your preferred outbound and inbound flights, Google will also show you how the fare changes for different tiers of tickets – economy, premium, business, first – as well as what benefits come with each, such as free seat selection, number of free bags, and priority check-in and boarding.

There are some major airlines that are not included on Google Flights, such as Southwest, Air China, and China Eastern. That being said, Google Flights is still a good (if not the best) place to start and sufficient for most trips.

Kayak

Kayak is a flight search engine that is most helpful when there is flexibility in your travel schedule, and you want to compare the lowest prices from both airlines and OTAs. It also offers an option called “Hacker Fares” which combines two one-way tickets from different providers to get the best price.

Momondo

Momondo has a user-friendly interface that features pricing trends to allow quick and easy date adjustments to get the best price. It also offers a Hacker Fare option that combines one-way tickets from different providers to get the best price.

Skyscanner

In addition to all the basic search features, Skyscanner offers the very helpful ‘Everywhere’ feature for exploring all available destinations and corresponding pricing for a given departure city or airport. It also has price alerts that will notify you if your preferred flight prices change. In our opinion, it is the most comprehensive flight search engine, along with Google Flights.

Scott’s Cheap Flights

Scott’s Cheap Flights is a hybrid between a flight search engine and a flight alert subscription. It allows you to enter your departure airport and will notify you when good flight deals are available from that airport. If you know your destination, you can also enter it and see what deals are currently available. The website claims that most deals are 40% – 90% off normal prices and in our experience that has been pretty accurate. Scott’s Cheap Flights offers three subscription tiers:

By now you should have narrowed down your options to a handful of flights that meet your preferences. Next, there is a couple of simple considerations that will help you further refine that list:

• Which airports are best for layovers?
• Which airline/aircraft provides the best in-flight experience?

Which airports are best for layovers?

Finding flights with the best airport layover options, including the airport lounges in those airports, is especially impactful for international flights with long layovers. Anytime you have the option to connect through one of the world’s best airports, such as Hamad International Airport in Doha, Singapore Changi Airport, or Tokyo Haneda International Airport, you should take advantage of it. These are playgrounds for professional digital nomads and the airport lounge options are usually exceptional.

We regularly fly between our homes in Miami, Florida, and Sofia, Bulgaria. Currently, there are two good flight options for that trip – Turkish Airlines with a layover in Istanbul or Lufthansa Airlines with a layover in Frankfurt. The length of the layover and total flight duration is similar for both options; however, we normally book with Turkish Airlines because we prefer the Istanbul Airport and Turkish Airlines airport lounge (accessible with our Priority Pass Select membership we receive through our Chase Sapphire Reserve credit card).

The Priority Pass or LoungeBuddy websites and mobile apps are easy to download and very helpful for quickly finding and ranking airlines lounges by the airport.

which airline and aircraft provide the best in-flight experience?

The airline and type of aircraft you fly on can have a huge impact on the quality of your travel experience. For example, whether your flight has video screens, USB plugs, and Wi-Fi varies by airline and aircraft.

Additionally, booking a flight that isn’t crowded, has your favorite seat available, is likely to upgrade you, or can be booked with frequent flyer miles is information you may want to consider before booking your flight. Airlines make some of this information available, but there are a couple of websites that specialize in these types of insights.

Expert Flyer

Expert Flyer is a subscription service that provides real-time data from hundreds of airlines, including seat maps, award availability, and seat reviews by fellow travelers.

Under their free subscription plan, Expert Flyer will notify you when a better seat becomes available on a given flight. The paid subscription plans provide a long list of flight-specific data, alerts, and services that can be very useful to frequent travelers, especially those looking to book with points or score free upgrades.

Seat Guru

Seat Guru provides free seat maps, details on in-flight amenities, and seat reviews from fellow travelers. Additionally, they provide helpful information on baggage allowance, flying with infants, and traveling with pets for over 100 airlines.

Related Post: The Ultimate Guide to Airport Lounges

We like to think of frequent flyer miles and credit card points as special currencies that can be used to pay for all sorts of travel expenses. Deciding when to use them instead of cash is an important consideration and depends on availability.

There are two primary ways to pay with miles and points – book directly with an airline using frequent flyer miles or use credit card points as cash. We break down the pros and cons of each below, but our rule of thumb is to only book a flight using miles or points if we find availability at a ratio of 100 points per dollar or less (e.g., 50,000 points or less for a $500 flight).

Paying with Frequent Flyer Miles

In many cases, flights and upgrades can be purchased with frequent flyer miles. Airlines limit the number of passengers they allow to book with miles for a given flight, however, so this option may not be available for your preferred flight.

The number of frequent flyer miles required for booking a flight is not directly tied to the price of the ticket but instead is based on the distance traveled. So, if we think of frequent flyer miles as a currency with an exchange rate of roughly 100 miles per $1, then a quick comparison of the cash rate versus the miles required will tell us if we are getting a good deal.

In one instance, we booked round-trip business class tickets to French Polynesia (priced at $5,000+ each) for 70,000 United miles (ratio of 14 points per dollar). That was a VERY GOOD use of miles. In another case, a flight to London required 100,000 points versus a cash rate of $800 (125 points per dollar), so we decided to pay cash and save our miles for another day.

It is important to note that while maximizing the use of miles is smart, airlines are constantly increasing the number of miles required for award tickets. As a result, the value of frequent flyer miles decreases with time.

Frequent flyer miles are usually earned only when flying with an airline, but if you have a travel rewards credit card you may also be able to transfer your credit card points to your frequent flyer account. Each travel credit card company has its own list of airline transfer partners and the typical transfer rate is 1:1 or 1,000 credit card points = 1,000 frequent flyer miles.

To search for award availability, create or sign into your frequent flyer account with the airline you are considering and search for your preferred flights. You will be able to search and filter for flights with award availability just as you would for flights with cash fares. ExperFlyer.com is also a great resource for finding award availability quickly across multiple airlines and flight times.

Paying with Credit Card Points as Cash

Flights can also be paid for with credit card points. Most travel reward credit cards provide the option to either pay with points when you purchase your flight through the credit card’s travel portal or apply your points as a credit towards travel expenses booked through a third party.

The exchange rate commonly offered by credit card companies is 100 points = $1. The two current exceptions to this are Chase Sapphire Reserve credit card holders receive an additional 50% bonus when booking travel through Chase with points and American Express Business Platinum cardholders receive 35% back when using points to buy a business or first-class ticket through Amex Travel.

Using credit card points as cash typically doesn’t maximize the value of your points, but it is a good option to have.

Related Post: How to Travel For Free – Miles and Points

By following the steps above, you should now know which flight you want to book. The next step is to determine WHERE to book your flight. Ultimately, there are only two places to book a flight online – directly with the airlines or through an OTA (note that we categorize credit card travel portals separately from other OTAs because they are worth distinguishing).

Flight availability, price or points required, change fee amounts, and quality of customer service all vary depending on where you book. Below is a table of how airlines, credit card travel portals, and other OTAs typically compare across these categories. We discuss the pros and cons of booking with each more below.

Airlines

In most cases, booking flights directly with the airline is the best option. It usually results in the best cash or award fare, has the lowest change fees, and has the best customer service.

When buying a cash ticket, using your frequent flyer number and a good travel or airlines branded credit card will ensure you still earn miles and points from your flight. For award bookings or award upgrades, you can compare availability across flights and quickly book using the frequent flyer miles in your account.

For any reason, if you need to make changes or have an issue with your flight, you can work directly with the airline rather than having to go through an OTA, which often has sub-par customer service. 

Credit Card Travel Portals

Credit card travel portals are usually the second-best overall booking option. The major U.S.-based travel credit card companies – American Express, Capitol Once, Citi, and Chase – each have a travel booking portal for their cardholders. In some cases, the credit card company is its own OTA – like American Express Travel – while for others the portal is powered by other OTAs (for example, Hopper is an OTA that powers Capital One’s travel portal).

Credit card travel portals may have less flight availability than airlines and other OTAs, but they reward cardholders with enhanced miles and points per dollar spent. Chase Sapphire Reserve cardholders, for example, earn 5 points per dollar on flights booked through Chase’s travel portal versus 3 points per dollar when booked elsewhere. Since users of the travel portal are also valued cardholders, customer service is typically much better than that of other OTAs.

Credit card travel portals can also offer features not available when booking directly through the airlines. For example, cardholders have the option of using credit card points to pay for travel purchases. Also, Capital One’s portal offers free price drop protection and price matching which ensures you get the best price available.

Other Online Travel Agencies (OTA)

Other OTAs are best for helping travelers make price-driven decisions. There are several reasons why OTAs can offer lower prices than airlines and credit card travel portals:

• They can combine the cheapest one-way fares on different airlines into a single ticket
• They earn commissions and pass them on to customers
• They take a loss on the flight in hopes you will also buy a hotel or rental car package
• They offer minimal customer support
• They get specific discounts from airlines
• They make it up with higher change/cancellation fees

Most flight bookings through other OTAs will still allow travelers to earn frequent flyer miles directly with the airline. Further, some OTAs also have their own reward programs that can be beneficial for travelers who plan to use a given OTA exclusively. The biggest challenge with booking through an OTA is that any issues related to your booking or flight are often more difficult to resolve. In our current era of flying, the likelihood that delays, changes, or cancellations occur is high, and having to resolve these with other OTA customer service departments can be time intensive and more expensive when making changes.

OTA examples:

• Agoda
• Bookings.com
• Expedia
• Hopper
• Hotwire
• Orbitz
• Priceline

We rarely use other OTAs for booking flights, so we won’t dive into each of those named above. In general, they differ slightly in the user interface and features but typically offer similar flight availability and pricing. Bookings.com and Hopper are the two that we have had the best overall booking experiences with in the past.

Finally, when it comes to purchasing your flight, using the right credit card can meaningfully decrease your ticket’s ‘net’ price. The table below provides a comparison of the best travel credit cards for booking flights across the booking options we cover above. Note, that many of these cards include additional perks such as Global Entry/TSA Precheck credit, free airport lounge access, and trip delay reimbursement.

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