What’s the Craziest Thing You’ve Done for Miles?

Million Mile Secrets asks what’s the craziest thing you’ve done to get a deal?

Maybe buying a year’s worth of toilet paper is something. Buying 12,150 cups of chocolate pudding (“Pudding Guy”) to earn over a million miles, and then donating the pudding was the stuff of legends, and even an Adam Sandler movie.

I’ve gone dumpster diving for Wendy’s soda cups and I went for a hair loss consultation with a full head of hair.

Wendy’s soda cups were good for free flights on AirTran. The Bosley hair loss consultation earned Delta miles. What have you done?

About Gary Leff

Gary Leff is one of the foremost experts in the field of miles, points, and frequent business travel - a topic he has covered since 2002. Co-founder of frequent flyer community InsideFlyer.com, emcee of the Freddie Awards, and named one of the "World's Top Travel Experts" by Conde' Nast Traveler (2010-Present) Gary has been a guest on most major news media, profiled in several top print publications, and published broadly on the topic of consumer loyalty. More About Gary »

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  1. Not for miles but status, I spent one New Year’s Eve going back and forth from DAL to AUS five times for segments on AA back in the day. (I started w 90 and needed 10) Five rounds trips with largely the same crew. Been EXP on AA for the 12 years since.

  2. Just the usual. An turnaround to Singapore from sfo and back. Just enough time to get off th plane and get a boarding pass. 4 times in one year. Everyone I know thinks that was crazy. But I know it’s nothing unusual tomobtain miles.

  3. I spent a lot of hours in 2015 driving around to Office Depots looking for $500 VISA gift cards when they had an instant rebate of $15 (or was it $30) off $600 in purchases which more than covered the activation fees. I bought tens of thousands of dollars worth on my 5x Ink card and then laundered them through Target’s Red Card. Also, did this with my wife’s card and to meet minimum spends on other cards. Those were the days.

  4. During my senior year of high school I spent a few lunches in the computer lab opening British Midland accounts in numerous fictitious names each of which earned a 1000 point account opening bonus. This was during the time of the BA/BMI merger so I could then create matching Executive Club accounts to transfer the points into and finally link these BA accounts to family pooling accounts each headed by a member of my family. Took my family on a few short haul AA and AS trips this way.

    Around the same time, Etihad had a BusinessConnect promotion that awarded 50,000 points for adding 10 (I think) employees to an account. Back to the computer lab and same story – 10 friends/pets/trees got Etihad Guest accounts attached to my BusinessConnect. Used the miles for my first trip in Etihad First CDG-AUH during my second month of college.

  5. Buying a $0.99 fishing line from Orvis to get a cheap partner for the AAdvantage 20k promo during the 20 year anniversary. A high school friend did the Latin Pass promo.

  6. When Aeroplan had a Grand Slam like promo, you could essentially get 17k free Aeroplan miles by pumping gas 35x or exchanging 1 US airways point on points.com for Aeroplan Miles. The best part was that you could pool Aeroplan Miles by converting them to Esso points and then back to Aeroplan. So I made many Aeroplan and Esso accounts, pumped a lot of gas before I realized the points.com method and Hundreds of thousands of nearly free miles were earned.

  7. Yeah, I guess the mint deal was the craziest. I wasn’t at “Mr. Pickles” level, but I was getting up there…

    But in 1983 or 1984, I may have done the first real mileage run. I did FLL-MIA-FLL 3.5 times to achieve Executive Traveler status on Eastern. L-1011 flights…

    Can anyone claim an earlier mileage run?

  8. Rented multiple cars without leaving the lot to rack up US Air grand slam “hits” AND talking my wife into doing it also. She thought it was crazy until we took business class to Rome and another business award to France on those miles. Gosh I miss off peak 60k business awards and the annual Grand Slam game.
    I remember my brother in law dumpster diving for kelloggs miles certs off cereal boxes also.

  9. Way back there was a Skippy peanut butter deal to earn companion tickets on AA (valid to Hawaii), there was a Bic razor deal that resulted in bags of donated razors, lots and lots of pudding, cases and cases of dollar coins, flying a $9 fare between Colorado Springs and Den, runnung around and checking into multiple hotels on the same night, renting numerous cars to barely drive them off the airport property to then go back hours later and return them all, some great stuff from Orvis, buying stacks of Wendy’s cups for our “family reunion”, hundreds of magazine subscriptions….need I go on? Can’t say there was any one crazy promo that really stands out. It’s been interesting for sure….

  10. I watched Zach Honig fawn over Brian Kelly for an entire flight to Hong Kong. Was disgusting and creepy.

  11. I paid for some food delivery with a card that earned 3 points (non-US program) via a website. Shortly afterwards, I was informed that the restaurant in question was actually closed and that I’d receive a refund.

    The card issuer rounded down for purchases when awarding those points, but rounded up for refunds when determining deductions.

    After auditing the last 2 years of account activity whilst armed with this knowledge of egregious awfulness I presented my findings to the issuer and obtained 27 points that were rightfully mine!

    (Also I was given another 10,000 points for finding the issue – only occurred for certain MCCs).

  12. I redeemed miles for United 2-4-2 Business Class. I admit its my fault and I need to repent.

  13. Three AUS-DFW roundtrips for Plat status with my wife in the early 2000s. There was some combination of very cheap fares and AA elite promo that I don’t quite remember.

  14. I used to do mildly obtuse things, like choosing OKC-CVG-ATL-LAS and LAS-JFK-ATL-OKC to pick up segments and miles. I’ve also opened checking accounts and test driven cars for miles.

  15. The craziest thing I’ve done is read this site multiple times a day… #rimshot

  16. I did the Bosley hair thing which doesn’t really seem crazy on the surface except I lived two and a half hours away from a Bosley location. And, funny how thinking patterns end up wired constantly toward miles/points accruing. As a result of this “hobby” I shop a certain way or select vendors based on ultimate advantages to me miles-wise. I searched around until I found a yard man who would agree to letting me pay him with gift cards from Office Max. Same thing with my cleaning person who comes twice a month. It took interviewing four different cleaners before I found one who agrees to be paid with a gift card. Then, there’s the dining program to which my husband will say to me, “Which restaurants are we allowed to go to?”

  17. I’m pretty tame so probably the most unique thing I did was the Cadillac test drive for 7500 AA miles…I online reserved a time for both me and my wife right about closing time at the local dealership. We walked in, the sales rep told us he didn’t have the car on the lot we wanted to drive and asked us if we were there for the AA miles. Yes…he tapped away at the keyboard, told us we’d been awarded our miles, and thanked us for letting him go home on time.

    The only other thing I’ve done was add segments…prices were similar and my employer didn’t care when/where I flew. Typically only an extra segment or two per leg but it got me DL status in the late 1990s…

  18. My daughter was very sick when she was born 20+ years ago. She thankfully survived and thrived. But I am never one to waste a crisis… The hospital bill was $150,000, and I decided I could take out credit cards to raise the mileage balances in our various programs by dividing up the payment as needed. The hospital refused. They did not want me to pay by credit card and get reimbursed by the insurance company. At the time, the hospital was required to charge a different rate if we paid cash versus the insurance company repaid them. I had no idea about the cost differential. But I told them if they didn’t permit me to do this, I was going public with this exciting information. The hospital relented with the understanding; this was a one-time exception. The law changed after that. But we traveled for years on those points.

  19. In 2001 Continental had several different promos with Amex for bonus flight miles. In turns out you could stack the various promos for up to 11x flight miles. I didn’t find out about it til just before expiration but was able to fly three round trips from DC area (can’t recall which specific airport) to Seattle over the space of four days. One of the trips was paid by work as I needed to make a site visit to a possible event venue, and I routed one itinerary through Orlando. So for a net to me of about $450 I earned close to 500,000 Continental miles and with a status match to Platinum from US Air Chairman’s I sat in first on 11 of 12 segments. Also spent one night at the SEA Hilton for a rate of $25 and met up with some other folks on Continental runs. Many nice redemptions out of that 1/2 a million mile score.

  20. ATL-ORD-DFW-HKG-DFW-ORD-ATL-DFW-ORD-NRT-ORD-DFW-ATL in sardine class to go from zilch to AA Platinum. The longest layover was 11 hours in HKG. Cost was just over $1000 including the hotel in HKG, a seriously sore butt, and a two-day travel hangover (fortunately on a weekend).

  21. In 1983, Pan Am flew a 737 shuttle from LAX to San Diego when they had 500-mile minimums. I did 4 turns on Christmas day and got over the threshold to get two first-class seats to/from Nairobi that were on sale for 100K miles each during the ’84 Olympics, where we escaped the expected mobs, bad traffic, etc.

    We were in tents in the Serengeti on a private photo safari, listening on my short-wave radio to events occurring a couple of miles from our home.

    Ironically, so many people left LA to avoid the Olympics crowds that the freeways were free-flowing.

  22. Many (okay, many, many) years back I was an assistant to an LAX-SYD frequent flyer (who along with @Gary taught me the miles game! A thankful & worthy hat tip to you both!). At the time, we were a small but active company and didn’t have company credit cards, so any expenses had to be put on our own cards and reimbursed. He allowed me to put all expenses I generated (office supplies, food runs, printing, lab costs, etc.) on my card and between the cc sign-up bonuses and meeting the minimum spend requirements, I was able to take one of my vacations during his employ in international business class using those earned miles, all without breaking a sweat. I was amazed to be in the upper deck business class section of a 747 in my early 20s headed overseas for less than the cost of a burger in miscellaneous fees! Okay, maybe not the craziest, but I never thought I would have 5 figure monthly credit card bills, be able to pay them off every month AND travel in luxury! Ha!

  23. In 1995, went around every Sainsburys supermarket in London buying £1,500 worth of Baileys Irish Cream and Andrex toilet paper. This gave us enough miles for two round trip tickets from London to LA in the brand new BA First. It was my first redemption flight and the beginning of a wonderful hobby.

  24. Wendy’s (but I paid the employees to collect for me), 8x rt daily Bos-Lax for an AA promo (was EP and got upgraded on all but two segments and met Ben Affleck), 3x back to back rdu- anc for AA EP. But best had to be promo with Eastern and Miami Hurricanes football team. 5k for each season ticket package. But they had a $99 family endone package that counted. Bought 100 and sold them at a discount and gave a number away to Boys & Girls Clubs. 500k which I used on CO first class to Europe a few times with my gf.

  25. I wish I could recall the details more specifically, but years ago MyCokeRewards had a deal with Delta that a certain amount of MCR points could translate into DL miles. While I don’t remember the math on that deal, I do remember my wife and I not only bought oodles of 12-packs of Coke but we shamelessly asked our friends for any codes from their Coke purchases and even more shamelessly talked one eatery we frequented into letting us have their Coke packaging instead of tossing it. Over time we racked up considerable DL miles. We still buy Coke but no longer participate in the MCR program.

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