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Aug 8, 2025
A Search for Award Flights
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Garden of Eden on the Road to Hana (Maui) |
Join me as I search for award flights!
Sample Desired Trip: Seattle to Chicago
Goal: To see if you can book an award flight (at the lowest points price possible) by transferring your UR points to one of Chase's transfer partners.
Prerequisites: A chunk of time set aside to sit down and do a bunch of internet searches AND you've signed up for loyalty accounts with ALL THE PARTNERS. Hyatt, United, Virgin Atlantic, British Airways, etc. It's free! This is an important step before you can book with points and miles!
Today's example is inspired by a last minute trip my friend wants to take in the next couple of weeks, so this method makes sense. But if you are in the planning stages of a bigger trip in the future, perhaps it makes sense to purchase one of these award flight search memberships for a couple of months once you're ready to book and then you can monitor the prices for a little while.
Step 1: Do a one-way search on Google flights with your desired destination and date.
The purpose of this step is not to book a cash flight but to explore the different itineraries available as well as your options with different airlines. Google shows the top flights based on price and itinerary. In this case, the three best flights are nonstop departing in the early afternoon, arriving in the evening, and cost about $320 for economy. We also have several airlines to choose from.
Step 2: Do the same search directly on airline websites.
Note: This example will focus on discovering your options when you have a fixed date. If you have more flexibility with dates, then you can use the the airline's search tools to look for the lowest points/miles prices over a period of time, such as one week or an entire month.
In this case, because we're working with Chase UR points, if you book directly with one of the airlines listed in the above screen shot, you are limited to Chase's transfer partners: Southwest and United. Unfortunately, these don't always have the best redemptions. Fear not! You may still be able to book the American, Delta, and Alaska flights using Chase Ultimate Rewards! I will get to that in Step 3.
Let's open a new tab and start with Southwest. I see the 1:10pm flight, which is listed #1 in the Google search screenshot above. It costs 24,500 points. I can already tell that this is a bad redemption/use of points, so I would not book this flight unless I had Southwest miles I needed to get rid of. How do I know it's bad? Because it's only a 1.3 cents-per-point value. ($320 cash price ÷ 24,500 points X 100 = 1.3 cpp) The goal is to redeem your points only when you can get AT LEAST a 2 cpp value. (More thoughts on that later.)
Now, open a new tab and let's check United. (Note: I've heard you shouldn't sign in to your United account when you do this search, so I didn't.) I spot the flight listed #3 in the Google search and it's 32,500 points, which is worse than Southwest, so that won't do. But did you notice that the redeye at 11:45pm is only 15K points? And it's also marked as a "Saver Award"? (More on that in Step 3.) Switching to my Google tab, I scroll down and find that the cash price for that flight is $320 for a Basic Economy fare and $365 for a regular economy fare. Because a United award fare is equivalent to regular economy, that's a 2.4 cpp value! If you don't mind a red-eye flight, this is a great deal!
Step 3: Check airline partners for even better deals.
Step 4: Repeat steps 1-3 for the return flight.
- One, skip the trip and save the points.
- Two, if you really want to make the trip happen, don't want to spend cash, don't mind using points (but want to spend the least amount of points possible), and you don't mind a redeye, book the United flights! If you average both legs, it ends up being a 2.1 cpp value. ($639 cash price ÷ 30,000 points X 100 = 2.1 cpp) Even the AA flight booked via BA for the outbound and the United flight for the return flight would be a 1.93 cpp value. Not bad!
- Three, book the outbound flight with points and just pay cash for the cheaper return flight a day later. That's still a savings of $365. Not bad!