The 11 Greatest Miles and Points Deals EVER

There have been many great deals over time, and they never last. The lesson is to take advantage of what’s offered, make use of the benefits, and expect to have to move onto the next offer that comes along.

For all of the many great opportunities that there have been over the past couple of years, probably the greatest ones are even better. The funny thing is that in my frequent flyer youth, I never even knew how great I had it!

Then again, it was 2002 before I ever saw my first 20,000 mile signup bonus for a credit card. And it was 2003 before I excitedly signed up for a 40,000 mile offer for a Northwest Visa that took 2 years to get all of the miles. Still, we had miles for long distance offers back then and those were super generous.

But here are what I believe are the 11 most generous offers I’ve seen. They don’t include 40,000 British Airways points for test driving a Jaguar, or dumpster diving at Wendy’s for Airtran flights. Because as great as those were, I don’t think they were great enough.

11. Free status offers for Marriott Gold, Avis Presidents Club, Virgin Gold, Hilton Gold, Continental Silver just for becoming an AT&T customer.

10. Class of Service Bonuses on Upgrades (Earn more bonus miles on United than it took to upgrade US-Hawaii, the upgrade more than paid for itself).

9. 1-800-Flowers 100 miles per dollar with Delta. On December 30, 2003 1-800-Flowers sent out an email saying they would award 100 miles per dollar spent on flowers. I assumed they had bought a ton of Delta miles which needed to be awarded or else they would expire. So they thought they would generate some cash with this rapidly expiring asset. The email was targeted, but anyone could use the promotion. And it wound up being much bigger than they anticipated.

8. Track-it-Back. In the fall of 2009 US Airways offered a 250% bonus on points earned through their shopping partners (up to 10 transactions) as long as you made purchases from at least 5 different merchants. Track-it-Back sold their stickers with 40 miles per dollar which became 140 miles per dollar, or just over 7/10ths of a cent per point. Donate the items, and reduce your cost basis further.

7. Double, triple, quadruple bonus dipping (Continental, US Airways). About 13 years ago some members earned six-figure mileage flying cross country on Continental. Once upon a time you could fly just a handful of flights and earn Chairmans Preferred (100,000 mile flyer status) on US Airways. US Airways had no way to tell if you were targeted or not, so they posted on Flyertalk that people who weren’t targeted and signed up anyway would get in lots of trouble (hoping to scare folks off). Didn’t work…

6. Savings bonds, travelers checks, prepaid visa debit cards and the US mint. Over time there have been huge opportunities to buy money with your mileage earning credit card, at little or not cost, and then pay off your credit card with the money you purchased. Rinse, repeat. Whether savings bonds, travelers checks (thanks, AAA!), or visa debit cards which you then turn into money orders, these eventually get shut down — because the company offering them winds up eating the credit card transaction fees without generating real business or over concerns of fraud. But many frequent flyers have earned many millions of miles.

5. KLM Status Match and Millions of Free Miles: In the Fall of 2001, KLM wasn’t just matching status — they were matching the account balances in your competitor elite account as well!

4. LatinPass 1,000,000 Miles: During the first half of 2000, you could earn a million miles (with the dreaded LatinPass program) for flying a total of 9 international segments on 9 different partner airlines.

3. InsideFlyer-Starwood. In the Spring of 2002, Randy Petersen was giving away 2500 Starwood points with each Inside Flyer magazine subscription. Back then Starwood points converted 1->2 into Qantas, including bonuses. 52,500 Starwood points yielded Qantas points. Doing the math, it was possible to buy 21 Inside Flyer subscriptions, transfer the Starwood points to Qantas, and redeem for travel on the Concorde. Donate the magazines to charity and further reduce your cost basis.

2. Goldpoints/valumags: Around Christmas 2001 it was possible to earn more than 100 miles per dollar with your choice of several airlines by purchasing magazine subscriptions from Valumags through the Goldpoints shopping portal. Some members donated the magazines to non-profits for the tax deduction, reducing their cost basis even further.

1. Pudding Guy. Enough said. The dude is famous.

What great mileage deals, on par with these, am I forgetting about? Hit the comments and let’s build a better list.

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, 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. Thanks for the walk down memory lane.

    Anyone remember the $2.00 USAirways fare to ART (Watertown NY)? I did a couple of those when I was in LA for a biz trip. Credited the miles to UA.

  2. What one match my miles. I got a personal and a business card each for my wife and myself. Over $4k in travel credits.

  3. Yeah, I’m with beachfan on that CapOne deal. Very lucrative, very flexible, and very easy.

    There were also some crazy ways to redeem modest amounts of Citi Thank You points for crazy expensive biz class tickets that you then cashed in for “real” tickets. Folks got thousands and thousands of dollars of free travel that way.

  4. If you want to go old school, back in the 80’s, TWA used to let you accrue frequent flyer miles on free tickets.

    Combined with (IMHO) the greatest reward in the history of frequent flyer miles – 50K miles for one free transatlantic F ticket and an upgrade from Y to F, and it was essentially a perpetual motion machine.


  5. LatinPass required ten airline segments on LatinPass member airlines and a variety of other tasks.

    I posted the offer details in post #55 of the FlyerTalk thread you linked.

    Three other lucrative airline offers were 1999 OneWorld 100,000 miles for flying five member airlines. That offer could be earned with several airline frequent flyer programs. That was my first set of mileage runs and I made some mistakes with ineligible booking codes and the fact that Canadian Airlines was acquired by Air Canada ended up in my getting only 300,000 miles instead of 400,000 miles on $2,000 in flights.

    2002 was Star Alliance 5th anniversary for 55,555 miles flying five partner airlines. I purchased five 4-segment tickets and earned the bonus in four frequent flyer programs including Air Canada, Mexican, ANA and Lufthansa. My wife and I vacationed around Europe in London, Belfast, Amsterdam, Frankfurt, Munich, Vienna and Budapest and earned nearly 500,000 miles. After some voluntary bump vouchers the cost of our tickets was only about $1,200.

  6. What about 250 LifeMiles for making a 74-cent purchase on (donate shampoo to further reduce cost basis) or a $1 donation to PetSmart Pet Charities (same)? Those were a great deal. Plus, LifeMiles has some great redemption partners for domestic travel!

  7. Jan 2012, AA, TEQM ORD/DFW to SFO or LAX. Got as low at $79 each way ORD-LAX. 11 RTs = EXP for 2 years+.

    With 10%-off AA gift cards from Costco and 5-10% AA discount codes easily available, got the price under $1400, plus you got a ton of miles.

  8. Suntrust’ ORIGINAL Delta Debit card offer was pretty dang lucrative. 25,000 DL miles for $75 card fee. .3cpm! And that was back before SSN requirements. My dogs had Suntrust cards.

    I have very fond memories of US’s Grand Slam promos. Those were probably the most gameable promos ever. I really loved trying to figure out the cheapest partner activities. I still have some TIB tags around somewhere…

  9. My hero was the guy who bought TWO Freedom Passports from either Eastern or Continental for $1700 or so each. Each one allowed you to take a one-way trip each week anywhere in the system for 52 weeks, so two of them allowed a round trip each week. No capacity controls, and the trips earned miles. Then came triple miles in 1988 and his Freedom Passports were a bonanza.

  10. Any honorable mention for the Mypoints-Opensky deal in 2012? I don’t remember the details, but for $500, I got a bunch of decent kitchen stuff and I think around 75K United miles.

  11. 1) Mexican hat dances
    2) UA SYD C mistake fare in 2006. I locked up BD gold and 1k for the cost a few comfy vacations
    3) NH used to sell really cheap cash-for-upgrades on domestic sectors, including Okinawa runs. They would credit in most programs as full F.

  12. The Capital One match was great. 100,000 “points” for matching a bunch of Alaska Air miles I’d accumulated for the AK VISA credit card spend over the years and not a mile of flying. True, they’re not that valuable, but when we take our dream-trip they’ll be put to good use.

  13. Why pray tell has pudding man ever been invited to the podium at FTU? That’s just wrong………I think a ticker tape parade is more in order…….

  14. Back in 2012, you could obtain a 20% bonus for sharing miles and obtain 10,000 IcelandAir Saga points per ~$25 transfer fee. Canadians with an Avion credit card could utilize Avion bonuses at the time and transfer this into AAdvantage via and Esso Extra for free and obtain 7,800 AAdvantage miles or 9,000 BA points. I earned hundreds of thousands of miles this way . About $320 per 100,000 AA points. See here for some info:

  15. Not as lucrative as some of these posts from memory lane, but the MCI and Sprint bonuses were nice. I think one was 5,000 miles per month for 10 months. Got me a Northwest J ticket to Europe – without ever flying Northwest for the miles.

  16. Another vote for Citi TYP. Redeemed 160K points for 2 tickets. Netted $16,200 in DL credit. Took me 3 years to blow it on many transcons and 3 biz tix on AF.

    About the same time they made the mistake of offering me 0% for a year on balance transfers. After moving credit lines around I took out $100K and put it in a Citi savings account earning 5%. Easiest $5K I ever made.

    And then I sold all my Citibank shares since I realized they were clueless.

  17. US Mint…dollar for dollar the best deal ever 🙂 My bank absolutely loved seeing me roll in with 200 lb bags of coins to deposit however.

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