What’s the Craziest Thing You’ve Ever Done to Earn Miles? Here Are Five.

I’ve done a lot of crazy things in my life to earn miles. I bet many of my readers have too.

There are things that some people only think are crazy — like buying coins from the US mint with a credit card, depositing those coins in the bank and paying off the credit card; like opening online checking accounts and funding them with a credit card (with banks coding the transactions as purchases) and using the new checks to pay off the credit card; like taking endless surveys or renting and returning cars that you do not need and don’t actually drive.

Then there are things that are actually crazy. Which ones have you done? What’s the craziest mileage-earning scheme you’ve taken part in?

  1. A Bosley hair loss consultation for 20,000 Delta miles.. I wasn’t the only one who went despite being far from bald.

  2. A Lasik eye exam for 5000 Delta miles.. I wasn’t the only one who went despite not even wearing glasses.

  3. Dumpster diving for Wendys sode cups when those were redeemable for Airtran A+ Rewards credits.

  4. Donating blood.

  5. Child support payments. Apparently Mastercard and Discover are accepted by Kentucky, Louisiana, Maryland, Maine, New Hampshire, New York, Ohio, Texas, and Wisconsin. (This settles a mystery of ‘what merchants take Mastercard but not Visa..?) Visa and Mastercard are accepted by Arizona, Illinois, and Pennsylvania. Surprisingly this revelation didn’t lead to a rash of frequent flyer pregnancies or divorces.

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. 1, 2, 4: Done.

    Convinced my office to allow me to put their holiday flights on my credit card one December–cranked out around 25K miles for that one!

  2. Greetings from our current Airtran flight.

    Dumpster diving for Wendys cups is by far the craziest thing we’ve done to earn miles/ points for a free flight. It is a great memory!

    Happy Thanksgiving.

  3. 1985: Took “3” segments FLL-MIA-FLL-“MIA” to maintain Executive Traveler. The third segment was enough, but would have stranded me in Miami without a car, and there was not a flight back until the next day. So I boarded the flight and then sneaked off. Obviously this was so far pre-9/11 that it wasn’t a big deal, whereas now it would be a major incident. Back then they probably just said, “Oh, we miscounted. Cleared for departure.”

  4. In 2006, I purchased $1000 worth of peppermint tea from a grocery store which ran a bonus points promo on it – these points converted into LX Miles at a very, very favourable rate.

    After clearing out the shelves of all stores in my region, I’ve moved on to buying an entire pallet from the distribution centre. The Salvation Army met me on site to pick up the tea for shelters. I got a tax receipt for my donation.

    Good ol’ times… 🙂

  5. Michigan takes child support payments via Master Card also. I’ve probably earned about 50,000 miles on my SunTrust Debit Master Card this way.

  6. A MR in 2005.An AA Promo.
    I did 6 RT flts.DFW-AUS in 3 days, plus , had to do
    I got 85K AAdvant. miles.
    The highlight was meeting RANDY plus a CNN reporter and
    cameraman on one of the flights.

  7. Buying 1,700 cups of Healthy Choice chocolate pudding in 1999 for about 120,000 airline miles.

    Taught elementary summer school and let 30 kids eat all the pudding they could stomach.

    Back in 1999-2001 when miles were earned from places like MyPoints and many other sites for clicking online ads, I would spend about an hour or two a day clicking ads in a computer lab with 12 computers.

    I picked up a million or more miles that way.

  8. A box containing $10,000 full of worthless Trackitback stickers is sitting in my office, mocking me. The 1.4 million US miles however are not.

  9. I went to a brothel in Dublin once on St. Patrick’s Day and was offered 100 Membership Miles AMEX points per US$ spent. And there was a special that day. I spent $250 and got 25000 points plus a very amusing and satisfying time.

  10. I collected Coke bottle caps in the early days of the program (no restrictions). I had a couple of customers who operated a bottle redemption center and bought bottle caps for a penny a piece from them.
    I opened accounts for every family member I could think of (13)and patiently entered 30 bottle caps for each account per day. I got pretty good at it and could enter those caps in 1 1/2 hours. All those points were forwarded to my Delta, Hilton and IHG accounts since there was no restriction to where they were deposited.
    I realized enough points and miles for a 6 day hotel redemption in Europe and 2 coach tickets on Delta.
    I can also relate to Ric Garrido and his Mypoints redemptions. I also participated in this program and have pictures of the gift cards, hotel certificates and Airline mile statements from this program as well as other less famous endeavors before the dotcom bubble burst post 911.
    Those programs have been diluted over the following years but they still provide pleasant memories of what the world wide web was when companies were exploring different ways to get someone to visit their website, paying them significant amounts of cash, miles and points to introduce them to their advertisers.
    It was these programs that got me started in the hobby I enjoy today.
    Those were the good ole’ days.

  11. Racked up over 100k of miles in AeroplanStarChallenge simply by converting 30-some Esso points to Aeroplan for 16,500 miles each Esso card. It was tedious.

    Then transferred miles constantly between Icelandair accounts when they offered a 20% bonus all for just a $30 fee per transfer. Also over 100k transferred to AA via Esso Extra.

  12. Back before I ever read a points/miles blog (about 2-3 years go), I thought I was so clever coming up with my own ways to earn lots of miles. Back then I only had Citi AA cards and Amex Platinum. I use to churn the AA cards before I knew what churn meant every few months (personal/business for me and my husband)….so lots of AA miles. Became AA Lifetime Platinum without paying for AA tickets. I used to buy gift cards ($100 was the max) at my local supermarket (back when they were paper (not reloading plastic) and loved when I’d stop in for bananas for .59 and get the remaining cash back. I had to stop at the back frequently to get rid of all the cash. I would buy $5-10,000 worth of gift cards at a time, gave them as gifts to everyone instead of cash, which I still do. I was sad to see the paper gift cards disappear. Now, after the few years of reading blogs, I have 17 active Amex cards (between me and my husband) and loaded with Chase cards, some Barclays, Southwest (which I don’t even like), some hotel cards. Wish I was in the game during the coins and online checking accounts.
    Just met an asst mgr from Office Depot at a friends house today….first question was “is your store selling Whole Foods gift cards?”

  13. This is pretty tame compared to some of these (1700 cups of chocolate pudding? Amex points at an Irish brothel??, but the thing I have the most trouble explaining to my friends was taking the 5:45am 17-minute flight from HLN to GTF in the dead of December, sleeping in the airport for 4 hours and then flying back home — it was just enough to get me to Delta Platinum the next year.

  14. 10k Delta miles per car rental costing $30 with Budget and Avis. Racked up about 500k miles.

    How about 800k Dividend miles via TrackItBack promo for .70 cent/mile

  15. Did the Lasik thing…don’t wear glasses, but did learn a little from the exam.

    As to places that take MasterCard and not Visa, I was in a Sam’s Club in Colorado with some friends. They only had Visa and Sam’s Club didn’t take it, but I had a MasterCard they did take.

    Craziest thing…bought a room in a Hilton and gave it to friends so that I could have a room on my Hilton account that allowed me to do a Hyatt Diamond challenge.

  16. I just changed electric companies to the one that charges so much more that the 15,000 US Airways Dividend bonus miles after 2 months of continuous service has never been worth it in the long term. Until now, when I’m 3 months away from the closing date of selling my home.

  17. I have gotten up to 7 miles per follar spent at DFW and most other airports by using my Venture card to get double miles and registereing my card on http://www.thanksagain.com for miles earned at the airports for gifts for my nephews.

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