The 10 Greatest Airline Mileage Deals Ever—My 7 Million American Airlines Miles Only Ranks #2

I’m still working through miles from a shopping promotion in 2009. I generated 16 million of them across various accounts, buying stickers from a company that promised to help recover your lost belongings. Twelve years later, another promotion delivered 7 million American AAdvantage miles… and, unexpectedly, the airline’s invitation-only ConciergeKey status. Neither gets first place on this list of 10 greatest mileage deals of all time. Greg and Nick’s latest Frequent Miler on the Air episode, about their biggest points gambles, got me thinking about updating my list of the greatest mileage deals of all time. Some of these were deliberate promotions. Others worked because nobody had thought through what would happen when customers combined the offers. And the #1 winner didn’t receive a single mile. #10. Two Cheap Hyatt Stays Bought 13,500 United Miles And A Free Night During the Great Recession, Hyatt was willing to give away an extraordinary amount to get people into its hotels. Faster Free Nights let you earn a free night after two qualifying stays, which meant you could stay cheaply and redeem somewhere expensive. In fall 2009, that combined with United mileage offers: 500 ordinary miles per stay, a 5,000 mile bonus per stay, and another 2,500 miles for every two nights. Two one-night stays produced 13,500 United miles and the free hotel night. The additional 2,500 mile offer topped out at 25,000 miles. I was finding Hyatt Place properties near Washington Dulles for around $60 on weekends. That meant roughly $120 before tax for the two paid nights, the miles, and a free night at a much more expensive Hyatt. #9. LatinPass Offered A Million Miles For An Airline Scavenger Hunt In the first half of 2000, a coalition of Latin American airlines offered a million miles for completing a fairly ridiculous itinerary: an international flight on each of its ten member airlines, three flights on partners, three hotel nights across at least two partner hotels, and five rental car days. Loyalty Traveler’s Ric Garrido recounted getting questioned by police in Quito after flying to Lima, back to Quito, and preparing to fly to Lima again on the same day. He handed them the promotion’s newsletter, with the Spanish version facing up. They didn’t read it. Long before the recent million mile airline challenges, people were piecing together trips on airlines they’d barely heard of to satisfy a loyalty program’s checklist. What keeps this lower in my ranking is that LatinPass made members fight to document their activity and made the rewards less useful afterward. #8. KLM Matched Your Miles, Not Just Your Elite Status After Belgian airline Sabena failed in 2001, KLM wanted its customers. They offered something far more generous than an ordinary status match: a match of your mileage balance, too. And it wasn’t limited to people with Sabena miles. There were eligibility and flying requirements. Steve Belkin described getting his 2.8 million United miles matched after meeting an eight segment KLM or Northwest requirement. The flights cost $1,100 and were travel he’d already planned. #7. Magazine Subscriptions Bought A Roundtrip On Concorde In June 2002, I wrote about flying Concorde for $1,258.95 in magazine subscriptions. Randy Petersen was offering 2,500 Starwood points with each subscription to Inside Flyer. You could buy 21 subscriptions for $1,258.95 and receive 52,500 Starwood points. Starwood added a 5,000-point bonus for each 20,000 points transferred, and Qantas had a generous 1-to-2 transfer ratio. Those 52,500 Starwood points became 125,000 Qantas points—enough for a roundtrip British Airways Concorde award. At the time, award availability wasn’t much of a problem. Concorde retired the following year. This bought access to an experience you can’t buy at any price now. #6. Goldpoints And ValuMags Sold Cheap Miles You Could Send To Different Airlines Around Christmas 2001, the Goldpoints shopping portal offered a promotion on magazine subscriptions through ValuMags that worked out to more than 100 airline miles per dollar. Goldpoints was the odd shared rewards program of Radisson hotels and TGI Fridays. The hotel version had the better airline transfer terms. I bought heavily through the portal, acquiring transferable rewards for less than a penny per airline mile at a time when award charts were far more generous. The ability to choose the airline made this especially useful. You weren’t committing all your travel money to one program’s award availability. The transfer rate was subsequently cut in half, and the shopping portal eventually disappeared. #5. The U.S. Mint Let You Buy Money With A Credit Card The U.S. Mint wanted dollar coins circulating. They sold the coins at face value, accepted credit cards, and shipped them for free. Buy $1,000 in coins, earn your card’s rewards, deposit the $1,000, and pay the credit card bill. I first wrote about this in 2008. The Mint kept changing the order limits, but for a time the opportunity was effectively unlimited. Some people bought seven figures’ worth of coins. Of course, putting the coins straight back into the banking system didn’t accomplish what the Mint wanted. It was also a lot of work for the customer: heavy boxes, deliveries to track, and repeated trips to the bank. But there was no merchandise to resell at a loss. You got your purchase money back from the deposit, and the opportunity lasted in various forms for about three years. #4. Pudding Guy Turned Dessert Into More Than A Million Miles In 1999, David Phillips spotted a Healthy Choice promotion offering 500 miles for every ten product barcodes, doubled to 1,000 miles if submitted by the early deadline. The important discovery was that individual pudding cups, selling for 25 cents, each had a qualifying barcode. Ten cups cost $2.50 and earned 1,000 miles. Phillips bought 12,150 cups of pudding, going from store to store and arranging bulk orders. His total Healthy Choice spending was $3,140, and his mileage haul from pudding and other products reached 1,253,000. Then he solved the problem of getting all the labels off. He donated the pudding to food banks, which helped remove the barcodes. The donations also brought a tax benefit. More than a million of the miles went into American AAdvantage. Back then, those counted toward lifetime status, so he also became a lifetime Gold member. He became Pudding Guy, a legend of the frequent flyer world, and his exploit inspired the pudding scheme in the Adam Sandler film Punch-Drunk Love. #3. US Airways And Track-It-Back Earned Me 16 Million Miles In late 2009, US Airways offered a 250% bonus on miles earned through its shopping partners if you bought from at least five different merchants. The bonus was capped after ten transactions. Track-It-Back sold stickers you could attach to things you might lose. Someone finding the item could contact the company, which would help get it back to you. The company offered 40 miles per dollar. Add the holiday bonus and 40 miles became 140 miles per dollar. You could make small purchases from four other merchants, then make a much larger Track-It-Back purchase. That’s about seven-tenths of a cent per mile before any benefit from donating the stickers. I donated the stickers to charity. I generated 16 million miles across various accounts. My net cost was below half a cent apiece. US Airways miles were incredibly useful, too, with generous partner awards and routing possibilities. When US Airways and American combined their programs, the remaining miles became AAdvantage miles. #2. SimplyMiles Delivered 7 Million Miles—And ConciergeKey Status In December 2021, SimplyMiles offered a holiday bonus of five times the normal miles, on top of the regular earning. One offer awarded 40 American Airlines miles per dollar donated to Conservation International. That meant 40 base miles plus 200 bonus miles: 240 miles per dollar, or about 0.42 cents per mile. A $1,000 donation earned 240,000 miles. There were no stickers to store, magazines to distribute, or coins to carry to the bank. People understandably wondered whether it was a mistake. I asked American Airlines to confirm the actual math and they did. There was still drama. The offer ended early, and getting the miles posted correctly took time. I was missing a bonus of 1,000,100 miles before the last of my miles finally arrived. I earned 7 million miles. Then, in July 2022, I woke up to ConciergeKey status. Other people who’d generated huge mileage balances through the promotion received it, too. #1. Grant Earned Zero Miles And Met His Wife In 2017, the British Airways shopping portal offered 150 Avios per dollar for Match.com subscriptions. Grant, who writes Travel with Grant, spent $548.57 expecting about 82,285 Avios. That would’ve meant buying miles for roughly two-thirds of a cent each. He didn’t get them. He complained to British Airways and Match.com for months and eventually received a full refund of the subscription price. In the meantime, he decided to actually use the dating service he’d bought for the miles. A woman named Laura sent him a message. On December 20, 2018, he proposed in San Francisco. They married in Sonoma on July 27, 2019, with 170 friends and family there. Grant thought his travel photos might have been what first caught her attention. Greg and Nick brought this story up at the end of their podcast. I’m putting it ahead of seven million miles and ConciergeKey. The promotion failed to deliver its promised reward, Grant got his money back, but he still won. How I Decide Whether To Go All-In On A Deal There were a ton of other deals out there, from Emmi Cheese to easyCGI. They don’t all work out as expected, and you generally have to commit money before knowing how the company would respond. So I need to make a bet and know how much to commit, managing risk. Read the actual offer, including how the pieces combine. With SimplyMiles, five times the regular miles as a bonus meant six times the regular miles in total. With Track-It-Back, the number of different merchants and the ten-transaction limit were key. Save copies of the terms, your activated offers, and your receipts. If the deal lasts long enough, test the process before committing more, but deals can be pulled early. Look for confirmation that answers the specific question. American confirmed the SimplyMiles donation rate and the multiplier. That’s more useful than a generic assurance that eligible purchases earn rewards. Assume failure Merchandise may be returnable, but a return deadline can arrive before the mileage dispute is settled. Items may not arrive (in which case you’d be dealing with a dispute). A deal might get dishonored. Decide how much travel you can realistically prepay. For a deal to actually be worthwhile it needs to displace actual cash you’d spend, not just rack up points that may never be redeemed or even might expire. Set the dollar amount before other people’s purchases talk you into going bigger. A deal can be worth doing for $500 and not worth doing for $20,000. The second amount ties up more cash, takes longer to use, and leaves more exposure to changes in the program even if the deal works out. Someone else’s huge purchase doesn’t tell you what amount makes sense for you. Earlier this year, the British Airways portal’s 250 Avios per dollar Kate Spade offer ultimately paid out. Greg and Nick passed on it. That outcome doesn’t prove their decision was wrong based on the information they had at the time. I’d be much more willing to take a chance on a modest purchase of something I already wanted than on a room full of inventory I needed to unload. At the other extreme, a confirmed offer at a fraction of the value I’ll actually get from the miles can justify buying years of travel in advance. In the case of SimplyMiles, I had some assurances that the deal would work. Plus, it involved a donation from Mastercard to its preferred charity at Christmas. Things were going to be messy, because they were forced to go over budget. Someone had to own the mistake. But it was going to be difficult for them to walk away, and if they did they’d surely find a way to offer refunds. I figured downside was limited. That’s not always the case. Topics on this page