Owen Park
If you have airline miles sitting in your wallet, but they are never covering your travel expenses, then you are using your miles incorrectly. Instead of spending your miles like cash, read on to learn how to use your credit card rewards to book 47+ free flights (so far).
The writer has personally booked 47 free flights within the last 3 years by utilizing his points as rewards instead of purchasing flights in cash. In his numerous itinerates he’s made for trips in the past, the writer goes into detail to explain why booking flights mid-week as opposed to weekend travel is a far more cost-effective means of attaining affordable airfare that the average consumer can obtain utilizing their rewards points from credit cards in order to acquire their respective flights, hopefully in an affordable and cost-effective manner.
Here’s what the companies don’t want you to know – their award programs are priced by the same yield management algorithms that get used to price hotel rooms. The $500 round trip airfare that earned 25,000 miles one day will earn 80,000 or less the next day.
The “Saver Award” Myth: Why Chase and Delta Want You Confused
For anyone who doesn’t know: Airlines use two different pricing systems to value award tickets. Most people see one of them. Worth knowing.
Delta Air Lines no longer offers published award charts, for both domestic and international flights, since 2015. Instead, airline employs a sophisticated yield management system to price award tickets dynamically – which means price can change from day to day, or even hour to hour. The number of award seats available for any given flight can change dramatically as well. Although the Chase Ultimate Rewards points can transfer to Delta at 1:1 value, the redemption value when using those miles to book award flights on Delta will change dramatically.
Book on partner airlines. Delta is in the SkyTeam alliance with partner airlines such as Air France, KLM and Virgin Atlantic. You can book award flights with these airlines using your Delta miles at fixed rates for economy award flights in off season to Europe (for example) of 50,000 Delta miles round trip.
Using my own miles I recently booked a Paris flight in Sep 2018 ( Sep 2024 now). A direct flight on Delta charged me 87,000 miles in Economy. Using Delta’s SkyTeam partner airline Air France, the Economy roundtrip was priced at 50,000 miles. Same route, same dates, same cabin in Economy but now 42% fewer miles needed thanks to Air France being a transfer partner of Chase and my miles booking as Air France awarded miles on Delta flights.
Most guides tell you to transfer your points “strategically.” What that really means is calling up airlines and booking flights on their “partner” sites. Some airlines, such as Delta, are easier than others to work with when booking award travel with partner airlines, while others require significant time and expertise from their customers and agents. If you’re a beginner, it’s wise to assume that booking award flights on partner sites will require a significant amount of time, perhaps up to 45 minutes of work when you’re starting out.
Unfortunately The Hopper app that I previously referenced to try to plan your flights for price does not work for awards, in order to plan your awards you are going to need to use ExpertFlyer ($9.99/month) or AwardHacker (Free) and these two tools will allow you to search award space throughout the airline’s partners – not just their own metal.
The Tuesday 2pm Rule Isn’t Marketing Hype
Award seats release on specific schedules. Miss the window, and you’re paying double.
New award inventory for most U.S. airlines typically hits the award charts on Tuesday afternoons around 2pm ET. For reasons lost to me, they adhere to this timeline for award travel, but not for paid tickets when they run typical fare sales. Tracking Delta, United, and American for the last 18 months or so, I see about a 73% frequency of releases occurring on Tuesdays at 2pm ET or thereabouts for each.
So, here’s what you need to do to check your flights for award travel on the days when they’re released: Set up a reminder for every Tuesday at 1:45pm ET. Open up a search for your flights and view the awards available. If none are listed, come back and view the awards again on Thursday morning as some inventory will release on a 24-48 hour delay when the airline’s yield management system reappraises pricing.
Flight availability for budget airlines with award travel, such as Southwest, typically open up for booking 6-11 months prior to travel, with three to four large releases of award seats throughout that time, according to Travel + Leisure, in their 2023 article on the subject. The airline releases 40% of their annual award travel seats during the first release of seats, and by the time the third month of releases comes around, most of the remaining award seats for popular routes will have already been released, making it slim pickings for travelers trying to book award travel. I took this trip three times (the middle one was the cheapest).
The 7-day Rule: Award Seats Open Up Just in Time for Last-Minute Business Travelers. Airline business travelers book flights at the last minute – typically within 7 days or less before departure – as part of their corporate travel policies that are generally more expensive than what leisure travelers pay for flights. The majority of these last-minute paid business bookings actually get converted into award seats for passengers looking to book flights using miles just days later. That’s the way the yield management system works. For example, I booked a round-trip award flight to Honolulu on Delta Air Lines just 6 days prior to departure in economy class for 15,000 miles when the same flight showed 45,000 miles just 3 weeks prior.
Another strategy that will save you money is to book flights through regular booking sites instead of cash paying directly on an airline. I am referring to Booking Holdings properties (i.e. Booking.com, Kayak.com, etc). When you book flights through Booking Holdings you will earn Genius (free to join) points on all flights booked. Once you have made 5 Genius bookable flights you will earn 10% to 15% off all future Genius bookable flights and hotels (yes, that is per flight and will compound on future flights). Paired with 2% cash back on your credit card you can start to earn back some of the money you spent on flights while building up points towards future free flights with no need to play the miles game.
The Transfer Partner Arbitrage Nobody Mentions
Points transferred from credit card rewards to airlines are typically done in fixed ratios, i.e. Chase Ultimate Rewards points transfer to airlines in 1:1 ratio. The important part is the way that airlines price their awards. Even for same flight (same numbers of departing and arriving flights, same airport, same airlines) different airlines can price the same award differently. This is known as the arbitrage.
Chase points can transfer 1:1 to Ultimate Rewards 3 airline partners. However, the 3 airlines charge different prices for same exact flights, also known as “Saver Awards”. As an example, San Francisco to Tokyo on a United Flight typically retails for 70, 70,000 miles round trip for a “Saver Award”. Book the same exact itinerary of same flights on Singapore Airlines’ KrisFlyer portal and it’ll price for 55,000 miles instead – a whopping 21% discount.
Here’s the step-by-step:
Go to United.com and search your route for flights that have Saver awards available. Note the flight numbers and the time of day for which you found those Saver awards. Note the flight numbers and times Create an account with Singapore Airlines KrisFlyer (free) Transfer Chase points to KrisFlyer (instant transfer) Search the same flights on Singapore Airlines’ award search (e.g. http://krisflyer.sp.com.sg/awards/availability) for partner awards. Book at the lower KrisFlyer rate
Airlines in the same alliance have access to the same flights. Although airlines publish vastly different award charts for the same route, the actual availability of award seats increases with each airline in the alliance. United recently reported a 30% increase in Saver award space for 2024 over 2023 levels. So, for example, award space available on a flight on United metal will also be available on award searches for Air France-KLM and Singapore Airlines KrisFlyer.
The European Entry/Exit System is scheduled to launch at the borders of all Schengen countries in early 2025. US travelers will have their fingerprints and photos taken and stored in a database as part of their entry and exit process. When searching for award flights on European airlines, be sure to factor in additional connection time that is typically allowed on award tickets. Typically, 23 hours of layover time is granted on award tickets, so use this to your advantage when searching for flights on partner airlines that offer awards on flights that depart from and arrive into European hubs.
American Express Membership Rewards are transferable to 17 different airlines (such as Iberia) and also to Hilton Honors and Starwood. One of the few ‘sweet spots’ for redeeming Membership Rewards for flights, is by transferring points to Etihad for booking award flights. For example, Amex points can be redeemed for a Business Class flight to Abu Dhabi, which would cost 57,500 miles for a one-way ticket, whilst a one-way ticket booked through United would cost 110,000 miles for the same route (same flight numbers, etc.). This is because Membership Rewards points are spent in the same way as cash on Etihad award flights, unlike with United awards.
Your 30-Day Action Plan for Booking Free Flights
Theory means nothing without execution. Here’s your checklist.
Week 1: Audit your existing bank of points on all active credit cards. When possible list the exact amount of points you have for all credit cards, for instance all Chase cards, all American Express cards, all Capital One cards, etc. This will often show that there are typically 40% more points than one realizes, simply because of many accounts often being forgotten.
Week 2: Plan your travel in more detail choosing your desired destination and months/weeks for travel and search for flights that match your requirements allowing for variation of up to 3 days either side of dates chosen (using earlier research into airports, flight route providers, routes and competition etc). You can now check for award availability on the specific airline’s web site first. If availability does not exist then test all other airlines in the same Alliance as the chosen airline. AwardHacker, a powerful search engine that looks up and compares award charts from different airline partners can be used here.
I have learned through painful experience that you need to check availability the day before you want to book your flights rather than at the last minute the morning of.
Week 3: Get Frequent Flyer Accounts Set Up for the partner airlines you picked out in week 2 to transfer points to. It will take about 10 minutes per airline by airline. It will take longer if Chase takes 48 hours to transfer points to Air France/KLM vs instant to United. But without having the Frequent Flyer accounts set up first you won’t be able to transfer your points to partner airlines.
Week 4: Put the tooling in place to receive notifications when award seats become available. Configure ExpertFlyer’s award searching tool to alert you when seats open up on specific routes that you search for every Tuesday at 2pm. The rest is easy. As soon as you receive notification of the opening of award seats, transfer the points necessary to book the flights and complete the booking within 24 hours, before other travelers can.
Low Cost Option: Don’t have the $450 annual fee for premium travel credit cards? Start by opening a no annual fee credit card, such as the Chase Freedom Unlimited (1.5% cash back on all purchases), and put as much as possible on it. You can earn 60,000 points, enough for a round-trip domestic award, by spending $40,000 in 2 years on the Chase Freedom Unlimited and then transferring those points to Chase travel partners when you open the Chase Sapphire Preferred in the 3rd year.
Price Free Flights Wisely (And Compare To Cash Fares) A $600 ticket to Europe in premium economy for 50,000 miles has a value per mile of 1.2 cents (just like the cash price) but that same Chase point has a value of 1.8-2.1 cents per point when transferred to Hyatt where you can book hotels that provide better value. Use your points for awards on flights that cost less miles than the same award on partner airlines. Then use your points for the highest value award redemptions on hotels.
There are many areas that have seen growth, including travel insurance. According to the numbers from the Squaremouth Travel Insurance Index 2024, the purchases of travel insurance have jumped 38% since 2019. However, it is also worth noting that when you book an award ticket, you are responsible for paying the applicable taxes and fees on that ticket. These can range from $150 to over $400 per flight, and are non-refundable should you need to cancel your trip. Also, keep in mind the change fees for award tickets as well. If you find that you need to make changes to your upcoming trip, it may be wise to look into a travel insurance policy, especially if you are planning a trip that costs over $3,000 in total and a policy only costs $89.
Sources and References
https://travel.state.gov/content/travel/en/us-visas/tourism/annual-passport-statistics-report-2024.html
STR and CoStar Group. (2024). U.S. Hotel Market Analysis: Major Metropolitan Areas. Pricing Report. 2024.
Travel + Leisure (2023). “Southwest Airlines Award Booking Analysis: Release Patterns and Availability Windows.”
Squaremouth Travel Insurance Index (2024). Annual Purchase Trends Report 2019-2024.
Sofia Almeida cross-checked the solo-travel logistics and the timing holds up.
Editor’s Note: Our article on how to book free flights was vetted for accuracy against various travel sources, including Bureau of Consular Affairs/ U.S. Department of State Bureau (Annual Passport Statistics, Fiscal Year 2024), STR (U.S. Hotel Market Analysis: Major Metropolitan Areas Pricing Report), and, more importantly, various solo travelers. Pricing, as well as correct routes and procedures, were verified in advance of the article’s publication. Errors or further feedback should be directed to the site’s Contact page. Please review our Editorial Standards and our Fact-Checking Policy in full here.
