My beginners blueprint to find the flight awards you want

TPG’s inbox is often overflowing with requests from readers who are having trouble booking specific award flights. Unfortunately, we can’t offer personalized advice to everyone, but we can direct you to the right on-site resources to help you plan the trip of a lifetime.

Today, I’ll walk you through my process for booking award flights, which is usually the first step in planning a points and miles getaway.

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Step 1: The where and when, but be flexible

Whenever I sit down to do flight award searches, I have a solid idea of where I’m trying to go and date ranges in mind. However, one of the secrets to my award-booking success is having a simple system for selecting backup destinations if I hit a snag and come up with no award inventory for any of the dates for which I can travel to my first-choice gateway.

Being flexible with the where and when is key. Of course, not everyone can be flexible with their dates; families and teachers who are tied to school calendars immediately come to mind. I’ll have a few tips for this group in the section below devoted to knowing when to start your award search.

Related: Getting started with points, miles and credit cards to travel

Pick your ‘where’

I have a Google Sheet that houses a list of the destinations I want to visit. It’s arranged by season, so I know which months are best to visit each place. That way, we don’t end up in, say, Bangkok on the hottest, most humid day of the year. I’ve been there and done that … and it wasn’t fun!

Here’s how to create your own “where and when” list. Refer to the following resources that outline why you should visit certain destinations at specific times of the year. Add the ones that tickle your fancy to your own “must-visit” worksheet.

• Best times for an African safari
• Best times for a Hawaii land trip and best times to cruise Hawaii
• Best times to visit Italy
• Best times to visit Japan
• Best times to visit the Maldives
• Best times to cruise the Mediterranean
• Best times to visit Mexico
• Best times to visit Spain
• Best times to visit Vietnam
• The best places to travel to in: January | February | March | April | May | June | July | August | September | October | November | December
• Where to go in 2025: The 29 best places to travel

One thing to note: I’m in my mid-50s, and over the last 30-plus years, I’ve been lucky enough to travel all over the world. That makes managing my spreadsheet easier than someone in their early 20s with a fresh slate of travel choices. After all, everywhere could make it to that list.

My spreadsheet only includes the places on my “visit someday” list and a few “greatest hits” destinations, like Bali, French Polynesia and Paris, that we’ll always want to visit when time and opportunity allow.

Some world regions aren’t represented on my spreadsheet. I spent more than a decade covering cruises and destination wedding travel, so I’ve been to nearly all of the Caribbean islands several times over. At this age, I don’t have a burning desire to return to any of these until I check off more of my “once-in-a-lifetime” destinations.

Your list can be as short or extensive as you wish. You want enough destinations on the list so you have a few options if your first-choice location isn’t aligning with flight award availability for the period you can travel.

Decide on the ‘when’

Now that you have a handy spreadsheet of where you want to go, decide when to travel. What destinations are listed in the boxes for those months? Pick one as your primary award search focus, but have one or two other destinations in mind if you can’t find the award flights you need at the points or miles price you’re willing to pay.

Don’t rule out traveling in the shoulder season (between peak seasons) or offseason, when award availability may be easier to come by. Just be sure you understand the trade-offs. For example, if you want to dive in Okinawa, Japan, don’t visit from November through February when the weather may be too cold and windy to spend time in the water. But, I traveled to Japan in early spring and was rewarded with beautiful sunny days and a morning of snow flurries, which was magical in Kyoto.

Related: Best times to book business-class award flights: Last-minute vs. advanced bookings

Step 2: Find the gateways that work for this trip

You know where you want to go. Now, you’ll look at the gateways that will get you there. This will help you select the points or miles you’ll use to get there, and we’ll talk about that in Step 3 below.

Not all loyalty programs are a perfect match for every destination. Before I pick which type of loyalty currency I’ll use — American Airlines AAdvantage miles, Air Canada Aeroplan points and British Airways Club Avios are some of my favorites — I research which airlines fly to my destination.

Start your search with FlightConnections. Type your airport code in the “From” field, leave the “To” box blank and hit “Return.” A list of nonstop destinations from that airport will appear on the left side of the screen.

Whenever I search for award space to a specific destination, I check which airlines offer routes from the airports I can reasonably depart from. I generally consider Hartsfield-Jackson Atlanta International Airport (ATL); Charlotte Douglas International Airport (CLT); Boston Logan International Airport (BOS); Dallas Fort Worth International Airport (DFW); Newark Liberty International Airport (EWR); Dulles International Airport (IAD) near Washington, D.C.; New York’s John F. Kennedy International Airport (JFK); Miami International Airport (MIA); Chicago’s O’Hare International Airport (ORD); Philadelphia International Airport (PHL); Montreal-Trudeau International Airport (YUL); and Toronto Pearson Airport (YYZ). If I’m traveling to Asia, I also consider connecting through West Coast airports, such as Los Angeles International Airport (LAX), Ontario International Airport (ONT) in California; San Diego International Airport (SAN); Seattle-Tacoma International Airport (SEA) or San Francisco International Airport (SFO).

You can also do this search in reverse, entering your destination in the “From” field and leaving the “To” field blank. Then, hit “Return” to see all the places with nonstop flights.

I don’t live near a major airport, so I always need to reposition to a hub city. You may or may not need to do the same. FlightConnections makes it a lot easier to visualize all my options.

Step 3: Determine which loyalty currency you’ll use

Once I see the airlines flying the route I want from one of these airports, I filter the list by airline alliance. That helps me decide what points or miles I’ll use for the trip. It also cuts down the list of gateways I need to search.

Here are the programs I generally use to book award flights within each airline alliance. Your list will be different based on the points, miles or other currency you have available.

• Oneworld: Alaska Airlines Mileage Plan, American Airlines AAdvantage or British Airways Club
• Star Alliance: Air Canada Aeroplan, ANA Mileage Club or United MileagePlus
• SkyTeam: Air France-KLM Flying Blue or Virgin Atlantic Flying Club

I also find excellent value for additional nonalliance awards when using Alaska Airlines Mileage Plan. Its roster of non-Oneworld partners includes Aer Lingus, Air Tahiti Nui, Condor, Hainan Airlines, Icelandair, Korean Air, LATAM, Oman Air, Porter Airlines, Singapore Airlines and Starlux Airlines.

I like using these programs for four reasons:

• Ease of earning points, miles or Avios within the programs
• Ability to transfer flexible points or miles to most of these programs from either American Express Membership Rewards, Chase Ultimate Rewards or Capital One
• Easy-to-navigate online booking platforms (for the most part)
• The value of the awards themselves (for example, I can book less expensive United Airlines award flights with Air Canada Aeroplan points than I can with United MileagePlus miles)

Step 4: Search for award availability

Searching for award availability is half art and half science, and it takes practice to refine your process. These days, there are a ton of excellent tools that will help you identify bookable award flights.

If you’re unable to find what you’re looking for on your own, try using one of these tools:

• Beginners guide to finding award space with ExpertFlyer
• The complete guide to searching award space on Roame.travel
• How I use Seats.aero every day to find the best airline award availability in seconds
• How to use the Points Path extension to compare cash and award rates in Google Flights
• Round-trip flights for under $150? Get discounted airfare alerts from Going

Related: Redeem your points and miles: How to search flight award availability for the major airlines

Step 5: Pivot to your second-choice destination, if necessary

If your award search for your preferred destination is a bust, it might be time to change course and consider your backup destinations.

Related: Avoid fees: How to change and cancel airline award tickets

Step 6: Book a flight (and maybe a backup, too)

You can always book something now and change your plans later if you find award availability for your first-choice destination. For example, I want to go to Bali in September or October but haven’t found the right award flights. I’ve booked a backup trip to visit Taipei, Taiwan, and Seoul, South Korea. If I end up finding award availability to Bali in that time period, I’ll cancel Taiwan and South Korea. Still, I’m happy to have travel plans in place in case I never find those flights to Indonesia.

Many programs, including American Airlines AAdvantage and Alaska Airlines Mileage Plan, offer free award cancellations. If you cancel before the first flight, you get all your points or miles and any fees back.

Step 7: ‘Garden’ your reservations, and improve them over time

Say you’re searching for Japan Airlines first-class awards to Tokyo using either American Airlines AAdvantage miles (an incredible deal when you can snag them for 85,000 miles one-way) or JetBlue TrueBlue points (185,000 points one-way).

You have your heart set on first class, but you’re only finding business-class seats on your preferred dates. Book them! Don’t let those coveted business-class seats get away. Book them so you know you have comfortable transit to Tokyo on the dates you want.

Then, keep checking for first-class availability. When you see it, call the airline and swap what you booked for the upgraded seats. (Note that you’ll need to pay any additional points or miles and fees at the time of booking.)

Also, keep searching for award flights on the days you booked. Sometimes, award prices go down. If that happens, call the airline to rebook at the cheaper rate and get those extra points or miles refunded.

I wish I could tell you the best time to search for flight awards, but it depends on the frequent flyer program, the destination, the cabin class, the number of tickets you’re trying to book and the season. You’ll need to research those factors to get a better sense of whether you should search right as bookings become available, any time between then and your preferred flight date, or at the last minute (like you would for a Lufthansa first-class award, for example).

Bottom line

Booking your first flight awards can seem daunting. However, I guarantee it will get easier, and you’ll soon have the confidence to perform regular award searches and find exactly what you’re looking for.

Just pack your patience. You won’t always find the perfect awards on the first try, but don’t give up. Sometimes, I find exactly what I need within the first few searches. Other times, it may take me weeks or even months, but that’s usually for more complicated itineraries or coveted first-class seats on a long-haul flight. In the end, you’ll find the best way to use your points and miles for your flights.