If you’ve never redeemed points and miles before, the whole process might seem daunting and nerve-racking.

  • Where do I start?
  • Do I have enough points?
  • How do I run award searches?
  • What’s my first step?
  • Do I book flights or hotels first?

You’ve probably seen words like “sweet spot” or “positioning flight” thrown around a lot. All the terminology and abbreviations seem like a foreign language or some kind of secret code.

One piece of advice I’d offer is to be patient with yourself. I promise it’s not some kind of secret society. You will soon learn the lingo and know-how to book your award flights with ease.

I’ve been doing this for a while, but sometimes, when I am putting together a big trip, I still feel overwhelmed and start thinking, “do I even know what I am doing?” So I take a deep breath and tackle the itinerary one flight at a time.

How Do I Start?

The first step is to create a spreadsheet.

Is there any problem that a good spreadsheet can’t help fix?

Actually, make that two spreadsheets: one with all the credit cards, points and miles that you have at your disposal and a second one just for places that you want to visit. Once you have everything organized, you’ll start feeling better.

I would like to offer one word of caution – don’t let the tail wag the dog. Figure out where you want to go first, and don’t let the points you have dictate your destination. In our awesome 10XTravel Insiders Facebook group, readers often list what points they have and ask what’s the best way to use them because they don’t have a destination in mind. There are so many places and countries to explore! Do some soul searching, talk to your family and your travel companions, and find a destination you all want to explore.

For example, if you’re thinking about Europe, let’s play (a sort of) game of 20 questions.

  1. Wine or beer?
  2. Nature or cities?
  3. Beaches or mountains?
  4. Outdoors or museums and culture?
  5. Warm weather or cooler temperatures or skiing in the mountains?
  6. Do you want to go to a more affordable country or maybe it doesn’t matter?
  7. Are the kids coming on this trip?
  8. Will crowds really bother you, or do you want to go to an off the beaten path destination?
  9. How important is food to you?

The last question is a trick question, of course. The answer should always be that food is very important! I mentioned food here because for me, food is one of the most important aspects of any trip. I also don’t want to pay an arm and a leg to get a good meal — I’m looking at you, Denmark!.

This elimination exercise can apply to any continent or destination. It’s very important to do some initial research and find the destinations and activities you like to do before trying to redeem points for travel.

Don’t just chase the perceived best value, but rather go where you really want to go!

How Do I Get There?

Now to the fun part – the award redemption!

I might be in the minority, but I love running award searches. First, I keep dreaming of the upcoming trip, the places I am going to go and the meals I am going to have there — have I mentioned food is important to me?.

Second, I love puzzles and I love seeing how everything starts to come together like a big puzzle. And lastly, think of all the cash you saved when you booked your award flights and spent very little money! Now it doesn’t seem like such a chore, does it?

So what is the best way to approach this? You just have to start running award searches. There’s no way around it and like with any new skill, it takes practice. Look at the 10X Travel articles that have the process broken down like Best Ways to Get to France or Best Ways to Fly to Dubai with points. Each one takes you through the award search step by step. We might not have the destination you want to visit yet, but the process is the same.

If you need help, our Editor in Chief Spencer Howerd has a dedicated thread in our Facebook group where you can ask questions about the best ways to use your points and miles for a trip.

Evaluate the options from your home airport. If you don’t live in an airline hub, it might be worth booking an inexpensive positioning flight to one of the bigger airports. Let’s face it, most of us don’t live near a major airport or an airline hub.

I fly out of a secondary airport, so I understand the pain. I sometimes have to book more complicated awards to or from Chicago (ORD) or one of the New York area airports, or work harder to find award space from my home airport. The extra work, or extra flying, is well worth it because it opens up additional possibilities.

My Favorite Tools

Google Flights

Google Flights is a great research tool. Before I start looking for awards, I want to see the possible routes to my destination. You can search by destination, multiple airports or even entire continents. I searched for a flight from Chicago to Europe and got this map that shows routes, stops and prices.

Award Hacker

Award Hacker might seem confusing at first, but once you get the hang of it, it’s an extremely useful tool. It’s not a perfect tool, but it’s good enough and a great starting point. I’m of the “don’t let the perfect be the enemy of the good” school of thought and I start with Award Hacker whenever I start a search for an award ticket.

Just enter your destination, preferred cabin and whether you want to search for one-way or round-trip award.

When you click on the blue arrow on the right, you can see all the other ways in which this tool can help.

Keep clicking on the little plus signs on the left to see step by step instructions. It’ll show you which airline award search engine to use, which transferable currency you can use and possible routes.

To be clear, Award Hacker doesn’t have the airlines’ live schedules like Google Flights. It also doesn’t know if award space is available – for that you’ll have to check each airline. Nevertheless, it’s a great starting point and a good road map.

If you want to see how award rates are set by airlines, check out our guide to award pricing.


FlightsFrom will show all the non-stop routes. It’s a great tool if you don’t want to connect and are looking for the fastest way to get to your destination.

Click on the Destinations tab to see more details.

Travel Portals: Chase, Amex, and Citi

Each major credit card issuer has a travel portal. Sometimes, booking flights through the portal might be a better option than transferring credit card points to airline partners. It’s important to always shop around first. You need to compare rates in the portal and the airline’s saver level award rates.

Airlines treat the tickets booked through the portals as paid fares, so you’ll earn miles on these flights. By booking a ticket on the travel portal you’ll avoid the biggest obstacle – award availability. This could be especially valuable if you have little or no flexibility or don’t want to spend hours searching for award space.

Chase Travel Portal

Booking the tickets through the Chase Travel Portal often might be the easiest, fastest, and cheapest way to a great redemption. You can often book inexpensive cash fares in economy (and sometimes even in business or first class) through the portal for fewer points than you would if you had transferred them to an airline’s frequent flyer program.

If you have the Chase Sapphire Reserve®, each point is worth 1.5 cents each. If you have the Chase Sapphire Preferred Card or Chase Ink Preferred card, each point is worth 1.25 cents each. If I hear of a great sale on cash fares, but don’t actually want to spend money, my first stop is the travel portal!

Amex Travel

One of the benefits of the Business Platinum Card from American Express is 35% points rebate for flights booked with Amex Travel. You’ll get 35% of your Membership Rewards points back for first and business class flights and for economy flights on your pre-selected airline.

This is a true rebate as you first need to have enough points in your account to book the flight. The rebate will post to your account in about 6-8 weeks after purchase. After the rebate, the value is similar to the 1.5 cents per point you get with the Sapphire Reserve in the Chase travel portal at about 1.53 cents per point.

The American Express Business Gold Card offers a similar benefit. You’ll get 25% of the points back for flights booked through Amex Travel. This is similar to the 1.25 cents per point value you get in the Chase travel portal with the Sapphire Preferred and Ink Preferred. In fact, it’s actually a little better at 1.33 cents per point.

If you find a good first or business class fare, it might make sense to book through Amex Travel. You might need fewer points after rebate than if you transferred Membership Rewards points to one of American Express airline partners.

Citi Travel Center

Citi ThankYou points can be redeemed at 1.25 cents per point through Citi’s travel center if you have the Citi Premier Card. Just like booking through the other travel portals, this might be a good option if there’s no award availability on the dates when you need to travel.

Travel Portal Advantages

Redeeming points through the portal is fast and straightforward. There’s no need to think about airline partners and alliances, how to search for award space and how to maximize every point and mile. I encourage you, however, to compare travel portal’s rates to award availability on airline’s site.

In the end, it’s all about comparing the number of points you’d need in a travel portal to the number of miles you’d need if you booked an award ticket. If the number of points/miles is similar, the portal will likely be the way to go for many of you.

Final Thoughts

If it’s your first time booking an award flight, take your time to learn about the best routes and the best reward programs to use. If you have a good stash of transferable currencies, such as Chase Ultimate Rewards or American Express Membership Rewards points, you are in great shape and can get practically anywhere in the world!

Check out one of our articles on the best ways to book flights to some of the most popular places around the world on the 10xTravel Destinations page. These articles are great for providing some ideas and detailed instructions on how to run award searches and on how to find the best value for your points.

You’ll be a points pro in no time!

Travel well,