One of the biggest challenges we hear from readers is how to book a full award trip. Putting together all of the pieces into a comprehensive trip can sometimes be overwhelming and challenging.

Although we strive to put together comprehensive content that shows you the step-by-step process of how to book with certain programs, like how to book a flight with AA miles, this doesn’t show the thought process behind the decisions. It really only shows how to book the flight if you already know you want to use AA miles.

Putting into words the conscious thought process behind booking an award trip is admittedly a challenge, but one that a reader said would be helpful. So I took the challenge.

Today, we’re going to go step by step on how I’d book an award trip using a real life example from a reader.

What Do We Have to Work With?

The first thing that you should do when booking an award trip is lay out what points you have to work with. This lets you know what options are on the table so that you’re not looking aimlessly.

In the case of our reader, here’s what we know:

There’s four travelers: two adults and two children. Our reader has two Companion Passes, one for her and one for her husband.

Our reader has 357,000 Southwest points and her husband has 332,000 Southwest points. She also has 50,000 AA miles and an AA companion pass certificate for one flight where she pays $99 plus taxes and fees. Finally, our reader has 687,000 Chase Ultimate Rewards points (nice job!).

We also know that our reader is looking to travel from Lubbock, Texas (to my dear reader: Hook ‘Em!) to New York City.

Armed with the knowledge of how many travelers and how many points are available, we can get started on the search.

Identify Potential Flight Options

The first step in booking your award trip is to identify potential flight options. This will help guide your search so you’re not looking in the wrong places.

Familiarize Yourself With All Available Booking Options

For our reader, Southwest is obviously a good option. They have two Companion Passes and plenty of Southwest points to work with. We also have a few AA miles and the companion pass certificate as well, so checking AA will be worthwhile too.

There’s also the opportunity to use Chase points with various Chase travel partners.

Chase partners with the following airlines. Since this is a domestic flight, it’s important to know which partners can book which airlines.

Chase PartnerAllianceAirline You’ll Fly
British AirwaysOneWorldAmerican or Alaska
Air France/KLM Flying BlueSkyTeamDelta
Singapore AirlinesStar AllianceUnited
United AirlinesStar AllianceUnited
Virgin Atlanticn/aDelta
Air CanadaStar AllianceUnited
Aer Lingusn/an/a
IberiaOneWorldAmerican or Alaska

Not all of these partners are created equally, and we’re not going to search each of them individually. Instead, we’ll return to this for reference later.

Keep in mind, this is just familiarizing yourself with all potential options. Knowing in advance what options you have to book your flight will help you target your search later.

Find Flight Opportunities

We’re still not looking for the award flights just yet. Right now, we’re going to find potential flight opportunities. You don’t want to waste your time searching for Alaska Airlines flights if they don’t even fly to or from your destination. Similarly, you don’t want to be looking for award flights that may have lots of stops or long layovers.

To help narrow this down, we turn to trusty Google Flights.

find flight opportunities in google flights

Plug in your starting and departure cities, along with your travel dates. Then, you can narrow down using filters to help find the flights you want.

For our reader, we’re going to narrow it down to “1 stop or fewer” and the duration to 8 hours. This will help us avoid any flights with really long layovers or multiple stops.

best departing flights

What we find is that American and United have a lot of options to get from Lubbock to New York with minimal stops and a relatively low travel time.

It’s important to remember at this step that this isn’t actual award availability – we’re just trying to get a sense of what flights we should be looking for in order to target our award search. Also, Southwest flights don’t always show up in Google Flights, so don’t discount Southwest just because it isn’t showing up.

Let’s summarize what we know:

  • Our reader has a good stash of Southwest points and Chase Ultimate Rewards
  • Our reader has a few American Airlines miles
  • In order to keep stops at a minimum, and a short travel time we should be looking for flights on either American Airlines, United and potentially Southwest

Taking this info, we can eliminate a few of the Chase airline partners from our criteria.

Chase PartnerAllianceAirline You’ll Fly
British AirwaysOneWorldAmerican or Alaska
Air France/KLM Flying BlueSkyTeamDelta
Singapore AirlinesStar AllianceUnited
United AirlinesStar AllianceUnited
Virgin Atlanticn/aDelta
Air CanadaStar AllianceUnited
Aer Lingusn/an/a
IberiaOneWorldAmerican or Alaska

Our next important step is to find the actual award flights of interest.

Finding Award Availability

We now know that we’re going to be looking for award availability on three airlines: United, American, and Southwest. Let’s go one-by-one to see what we can find.

United Airlines

One thing that can be a bit counterintuitive is finding the cheapest award space. If we went to United to search it would likely show us plenty of results. However, many of the results will be at higher redemption rates than we want to pay.

Although it is counter-intuitive, let’s search with a partner instead. Partner airlines will only show availability that is at the “saver” level, meaning that it requires the fewest points possible regardless of what program we end up booking with. This will help filter out the high redemption rates that we’d see by checking United directly.

For our search, let’s use Air Canada.

United Airlines using Air Canada - departing flight

With Air Canada, we can plug in similar criteria to what we did on Google Flights to help limit the results. Here, we limited it to “1 stop or less.” Air Canada doesn’t let us filter by total travel time, but we can sort the results by shortest trip, ensuring that the shortest travel times show up first.

finding award availability in united airlines with air canada

What we see is there are a lot of options on United with just one stop and relatively low travel times on the outbound flight from Lubbock to New York.

return flight with united from Lubbock to New York

However, the return flight has two stops and 19 hours of travel time! That’s a lot of time spent in airports and making connections that might not be so desirable.

So what we know is United has good availability for the outbound flights, but not so good for the return.

American Airlines

Similar to United, we’ll use a partner airline to find American airlines availability. In our case, we’ll use British Airways.

finding award availability american airlines using British airways

British Airways doesn’t give us the same options for filtering as Air Canada did, so you’ll have to work it out a bit yourself. What we find is that on the outbound flight, there’s an option with one connection in Dallas with a total travel time of 5 hours and 32 minutes.

finding award availability american airlines-flights with partner airlines

There are a lot of good options for the return flight as well, all with just one stop and fairly minimal connection times. Plus, British Airways shows us how many seats are available – with seven seats available this makes it easy to know there will be enough for everyone on the trip.

Now we know that American has good availability on both segments of the trip.


Finally, we’ll find flight options with Southwest. Southwest doesn’t have any partner airlines, so we’ll use Southwest’s site to directly see what flight options we have available.

finding award availability in southwest airlines

Southwest has quite a few good options on the outbound flight. We can eliminate one because it has two stops, and one option due to a long travel time of 9 hours and 40 minutes. This leaves us with two options on Southwest for the outbound flight.

finding award flight in southwest - return flight

For the return flight, all three options are a bit less desirable. They all involve either a relatively long layover time, or multiple stops. However, this is where a bit of judgment comes into place. We know our reader has the Companion Pass, so it will likely be far fewer points to fly with Southwest than another airline. We’ll determine this for sure later, but you might be willing to have a slightly less convenient flight if it means saving a chunk of points and miles.

Armed with this knowledge, we know that Southwest has a good option for the outbound flight, but not so good options for the return flight.

Summarizing the Info

Now we know what award flights are available that fit our travel parameters:

AirlineOutbound FlightReturn Flight

Now we can use this to target our final flight search.

Booking The Flights

Outbound Flight

All three airlines had good outbound flight options. With the goal of spending as few points as possible, let’s choose the best outbound flight option for our readers. This is where we can reference that chart again.

Chase PartnerAllianceAirline You’ll Fly
British AirwaysOneWorldAmerican or Alaska
Air France/KLM Flying BlueSkyTeamDelta
Singapore AirlinesStar AllianceUnited
United AirlinesStar AllianceUnited
Virgin Atlanticn/aDelta
Air CanadaStar AllianceUnited
Aer Lingusn/an/a
IberiaOneWorldAmerican or Alaska

For United, we can book using either Singapore Airlines, United or Air Canada.
For the American Airlines flight, we’ll be looking at British Airways or Iberia.
Southwest doesn’t have partners, so again we’ll only look to Southwest to book.


We already know that Air Canada will require 12,500 points per person for the outbound flight, so we can cross check with other partners.

booking flights outbound flights- united airlines with air canada

United will also charge 12,500 miles per person, but taxes and fees are less.

Singapore can be a bit tricky to search online. They don’t always load airports that aren’t major hubs. In our case, Lubbock won’t pull up online. When this happens, your best bet is to reference the award chart.

singapore airlines krisflyer miles award chart

What we can see is that flights within North America will require 25,000 miles round trip or 12,500 miles one-way.

So all three options are 12,500 miles, but the taxes and fees on United are the cheapest at $5.60 per passenger. In this case, we’d book with United directly. For four passengers that means 50,000 points plus $22.40 in taxes and fees.

American Airlines

From our handy chart, we know our options for booking a flight with American is through either British Airways or Iberia.

British Airways has some weird quirks to the search – you can only book for people in your friends and family account. If you haven’t set that up, it won’t let you search for as many tickets as you want. A workaround to this is to just search for one person, see how many seats are available (which we now know is seven), and do the math to figure out the total cost of the trip.

booking flights-outbound flight-american airlines with british airways

For the flight from Lubbock, the price is 18,500 Avios plus $5.60 per person. Four passengers means you’d need 74,000 miles plus $22.40 for all four passengers on this trip if you booked the American Airlines flight through British Airways.

Similar to Singapore for United, Iberia sometimes has troubles showing award availability.

book flights-american airlines-avios use table

Our solution is to go to the Iberia award chart. Iberia prices flights per segment, meaning each connection prices separately. To figure out the flight distances, we can go to the Great Circle Mapper tool.

great circle mapper tool

The first flight is 282 miles, so it would cost 6,000 miles per person. The second flight is 1,389 miles, and would require 11,000 miles per person. Your total is 17,000 miles plus the taxes and fees per passenger, or a total of 68,000 points for a family of four.


For our Southwest options, we’ll just go to Southwest and check the price in points for four passengers. Easy!

booking flights-outbound flight-southwest

Depending on which flight you choose, it will require anywhere from 10,716 points up to 14,576 points. The taxes and fees are $5.60 for all of our options.

Keep in mind that our traveler has two Companion Passes, so rather than multiply by four we’ll just have to figure out the cost for two passengers. Using Southwest the cost will be between 21,432 points and 29,152 points plus $22.40 in taxes and fees.

Putting It All Together

As you get this information, I’d highly recommend putting the cheapest option for each airline in one spreadsheet or table so that you can easily condense all the information into one place.

Traveling AirlineBooking ProgramTotal Cost
UnitedUnited50,000 points plus $22.40
American AirlinesIberia68,000 points plus $22.40
SouthwestSouthwest21,432 points plus $22.40

In this case, Southwest checks all the boxes – favorable travel times with minimal connections and the lowest points cost. Southwest is our winner for the outbound flight!

Return Flight

Now, we’ll do the exact same analysis for the return flight. Remember, however, that United wasn’t a good option for the return, so we’ll only look at booking the American Airlines flight with Iberia or British Airways and the Southwest flights based on our intuition that it will probably be a lot cheaper.

The good thing about this is, we’ve already done the work for British Airways and Iberia.

finding award availability american airlines-flights with partner airlines

All but one of our flight options is the same route, just in reverse. This means the cost will be the same to book it with either British Airways or Iberia. This saves you a lot of work, and now you’ll only need to check the Southwest options.

booking flights-return flights

For Southwest, the pricing is either 10,716 points plus $11.20 in taxes and fees or $12,260 points plus $5.60 in taxes and fees. This means your options will range from 21,432 points to 24,520 points in taxes and fees.

Putting this back into our handy little table, we can compare both options:

Traveling AirlineBooking ProgramTotal Cost
American AirlinesIberia68,000 points plus $22.40
SouthwestSouthwest21,432 points plus $44.80

This is where you have to make a decision for your personal travel plans. Would you rather spend 45,000 more points for the shorter flight, or save them and have a slightly longer layover? Making a judgment call like this is all up to you. Personally, I’d advise our reader to go with Southwest. Having 45,000 Chase Ultimate Rewards flights is worth at least $450, more if you redeem them for travel. That’s a lot of value for an extra two hours in an airport, but that decision will vary from person to person.

One Final Consideration

Now that we know how many points our reader needs to book with partners, there’s one final consideration: using the Chase Travel Portal.

Our reader informed me that they have the Chase Ink Business Preferred® Credit Card. Points associated with the card can be redeemed directly through Chase for travel at a rate of 1.25 cents per point. Before jumping on the Southwest options, we need to do a comparison of how many points this trip would take in the Chase travel portal.

This isn’t always a necessary step. If you’re trying to book an international flight in a premium cabin, you’ll rarely find the travel portal to be a better value unless there’s a good sale going on. However, I’d recommend comparing the price to the travel portal for all domestic flights, regardless of the class of service, and when you’re looking to book international flights in economy.

For comparison, we’ll be comparing our results in the travel portal to two options:

The first option is flying Southwest both ways. In total, our reader would need to spend 42,864 points to fly Southwest in both directions. Flying Southwest on the outbound and using Iberia points to book the American Airlines flight for the return would require 89,432 points.

Trip Summary

Choosing the cheapest round-trip flight that has a total travel time of less than 8 hours and only one connection requires 103,168 points through the travel portal. So that option is out.

But what about just the return flight?

trip review

The return flight on AA with just one stop and a short total travel time can be had for less miles than booking with a partner.

So how do we put this all together? Well let’s look at our table.

Traveling AirlineBooking ProgramTotal Cost
UnitedUnited50,000 points plus $22.40
American AirlinesIberia68,000 points plus $22.40
SouthwestSouthwest21,432 points plus $44.80

For outbound flights, it is pretty well settled that Southwest is the winner. It’s the cheapest option with just one connection and minimal travel times.

Traveling AirlineBooking ProgramTotal Cost
American AirlinesIberia68,000 points plus $22.40
SouthwestSouthwest21,432 points plus $44.80
American AirlinesChase Travel Portal51,584 points

Now, we can book the American Airlines flight for cheaper through the Chase travel portal. It still requires 30,000 more points than the Southwest flight, but it has about 3 hours less travel time with just one connection.

At this point, the choice is yours. Do you save more points but have a bit more inconvenient travel schedule with Southwest? Or do you book Southwest on the outbound and the American Airlines flight for the return? That’s a judgment call that you’ll have to make to book your trip.


Now that we’ve got flights squared away, it’s time to move onto hotels.

Similarly to flights, we’re going to start by taking a look at what hotels our reader can book with her points. As a recap, our reader has a ton of Chase points, so we’ll be looking at what hotels you can book with Chase points.

Chase partners with the following hotel chains:

  • Hyatt
  • Marriott
  • IHG

When it comes to hotels, I like to use Award Mapper to aggregate award hotels. While award mapper isn’t always up to date, it’s a good resource to visualize hotels for award bookings.

award mapper

Award Mapper makes it easy to visualize hotels available to book with points in one spot. You can also filter out chains that you don’t have points for and limit the number of points you’re wanting to pay.

Zoom in and hotels will start to populate on the right hand side of the screen. You can click on the hotel to be taken directly to that hotel’s website. Sometimes these links are broken, but you can just Google the hotel name to be taken there directly.

For our reader, I don’t imagine they’re wanting to burn all of their points on a hotel, so I’d limit the points needed to about 50,000 points per night. Keep in mind that with Marriott, your fifth night is free on award bookings, so a 50,000 point per night hotel might be a bit cheaper than it appears on paper once you factor in the extra free night.

New York being, well, New York, means there are a lot of hotel options. At this point I’d look at what hotels are in my desired location of the city, open the hotel website and look through pictures and room availability to decide what works best for you.

It might seem a bit vague, but choosing a hotel isn’t quite as methodical as booking award flights. There’s a lot of personal decision that goes into choosing the right hotel for your trip. Are you looking for luxury, or just a nice place to lay your head? Award Mapper can help you start by identifying hotels that you can book with points and narrowing it down based on your personal criteria from there.

Similar to flights, be sure to compare with the Chase Travel Portal as well. There will be hotel options in the travel portal that aren’t part of a major chain that you can choose from as well.

Final Thoughts

Phew, that was a lot, but now you should be able to replicate the process with your own trip in order to find the right flights and hotels for you. Booking your flights is a bit more methodical and a step-by-step process than choosing your hotel. Be sure to use the tools at your disposal to help narrow down your search for the right hotel.