The 15 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. I was constantly switching long distance carriers.

But here are what I believe are the 15 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. And they don’t include ‘mistake fares’, those are a whole different category.

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

14. 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).

13. 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.

12. Lifetime American AAdvantage elite status for credit card signups and spending. American used to count miles earned from any source towards lifetime elite status. That means just credit card signup bonuses and spending were enough to become a lifetime Gold (1 million miles) or lifetime Platinum (2 million miles). I hit my lifetime Platinum before becoming a regular American Airlines customer many years ago though. It’s been slow going since the change though it won’t be long until I hit 4 million miles – sadly that won’t get even 75,000 mile elite status. And unfortunately lifetime Platinum isn’t worth what it once was.

11. $2000 bought a free Presidential Suite night at the Fairmont San Francisco — and lifetime Presidents Club status unfortunately that’ll now be Accor status.

10. Citi ThankYou redemptions for $2700+ airline tickets. Years ago you could get Citibank to buy you a ticket at any price if you met the conditions of the Thank You points program. People would manage to buy themselves $8000 coach tickets to Japan, cancel, and retain the airline credit.

Not surprising that they shut down that sort of gaming by implementing maximum ticket values into their award chart. The sweet spot used to be redeeming for business class tickets inside the US and Canada at a value of 3 cents per point — 90,000 points bought a ticket of “up to” $2700.

The preferred airline to do this with was Delta, because their credits were eminently divisible back them. After booking the first ticket in your own name from the credit, you could use the balance on tickets for anyone you wished.

And with the Citi Drivers Edge card you could earn up to 6 points per dollar, matched by the miles you drove (so 12 points) and redeemed at 3 cents per point (a 36% rebate on gas and grocery store spend).

9. 13,500 United miles and a free night at any Hyatt for every two one night stays. Hyatt did some amazing things to put heads in beds during the Great Recession, stacking Faster Free Nights (once upon a time those were even earnable on Priceline stays, sigh) with generous United mileage bonuses.

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, 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 or travelers checks (thanks, AAA!), 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 at least one international segment on each of the ten LatinPass member airlines, flying at least three segments on partner airlines (KLM, US Airways, TWA); staying at least three nights in at least two partner hotels and renting a car for at least five days from their car rental partners.

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 plus bonuses. 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. He was even memorialized in the PT Anderson – Adam Sandler film Punch Drunk Love.

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 »

More articles by Gary Leff »



  1. AAdvantage miles by buying Nutri Grain bars. Bought several pallets of 500 mile packages at Costco, then used Publix doubler coupons. Earned 2MM ( lifetime Platinum) for less than $10K net after charitable deduction for donating bars to food banks.. Those were the days…

  2. How about taking a really old school—. When MCI/ATT/Sprint would call you up and offer you up to 50k to switch long-distance carriers for four or five months, then you switched again.

    Considering the long-distance rates and quality were essentially stream-lined back then, it was really like free miles to do nothing except hope you were home when they cold-called you!

  3. I’m still eternally grateful for the Hyatt Paris etoile mistake rate you published a while back. 2 separate weeks for only $21/night. My parents are also eternally grateful as they took the 2nd week I booked since my dad and I share first names.

  4. BMI, every 2 nights at Wyndham , 5000 miles including super 8, most super 8 in Asia $10 per night………..

  5. In the mid-1990s Continental offered a lifetime pass to their airport lounges for $1,000 for people over age 60. I took advantage of this just before they raised the fee and feel it’s one of the biggest bargains I’ve ever had since I still have the privilege with United Lounges as well as all other Star Alliance airline lounges.

  6. Around 1988, Southwest had a promotion with Burger King. Buy a whopper meal and get a free r/t companion ticket.

  7. Opening bank accounts up to 100,000 with a credit card and having it treated as a purchase

  8. Some honorable mentions:

    The US Airways hop, skip jump promo to chairman.

    The US Airways grand slam.

    Club Carlson 2 for 1 with the credit card.

    But, by far, the most lucrative for me was the brief and shining moment where the all stars aligned for about 5 weeks. I had a citi card that gave 5x at drug stores. Around the same time, CVS went from being cautious about vanilla reloads to changing their policies to allow up to $5,000 to be purchased at a time. I had one CVS and one cashier that had a box of blank reloads and I’d buy $5,000 per day and pay down my citi card back when vanilla’s were easily to liquidate. I earned something like 800,000 thank you points almost overnight until it came crashing down.

  9. Buy a one way ticket for $49 on Southwest to Cleveland, Nashville or Indianapolis and receive a one way rapid reward when exiting the flight. Ticket brokers hired people to fly the SAT-BNA-CLE-IND-CLE-BNA-SAT route daily for several weeks.

  10. In about 2004 I took advantage of some crazy Hilton bonuses that allowed me to be checked in over the phone at some Hiltons with $37-40/night rates. Those in turn yielded a bunch of bonuses. I redeemed the points for a safari for two back when you could use Hilton points for a package that included the Nairobi Hilton and several nights at Salt Lick Lodge. (Including meals and game drives!) It was such an insane deal that my husband was convinced it was a scam literally until the Hilton had someone to pick us up at the Nairobi Airport.

  11. Triple miles on all flights circa 1987-1988
    Included 3 x 1000 mile per segment minimum on Eastern and Delta connections.
    Combined with Eastern Airlines Weekender club and cheap car rentals.
    Made many trips from EWR to south Florida in those days.

  12. Free scratch off ticket for every passenger when Texas Air rolled everything Into Continental and had a service disaster in about 1987. Probably just EWR departures. Each scratcher had 20 cities.

  13. Fly 20 domestic segments on Delta, get a free business class ticket to Asia in about 1996. I did several 4 segment trips from EWR to Florida and Vegas. Shortest segment was FLL to MIA. I made all the bookings through Eaasy Sabre on prodigy or compuserve.

  14. not a public deal per se, but through sympathetic agents and leveraging their stated benefits, i’ve gotten agents (of one of US3) to continuously extend an award ticket originally redeemed in mid-2015 to be finally flown in Nov 2017 … all while incurring zero change fee, zero redeposit fee, me with zero status, and didn’t even have to use a lie

  15. When Starwood and Marriott first got together…..You could convert SPG Points (90,000) to Marriott Points (270,000) AND purchase a Marriott Travel Package with 120,000 Southwest Air Miles…..AND GET A SWA COMPANION PASS FOR TWO YEARS for free! So, for 90,000 SPG points you get …. 7 nights in Marriott Hotel AND 120,000 Southwest Miles, AND 2 years of Southwest Companion Pass. I rate this close to number ONE.

  16. The Mint coins were crazy. The UPS would come to the door every day with several hundred pounds of $1 coins on a cart, then I’d spend the afternoon going around to about 15 bank branches to deposit them, then pay off the credit card early and over pay, so I had a credit for the next order.

    The Ritz-Carleton 140k was nice. If you set the credit limit to $1k or less, they wouldn’t charge you the annual fee and you still got all the other goodies.

    The Capital One match promotion was great. They would match the number of miles you had sitting in your airline account. My wife and I had about 400k in each of our Delta acts at the time. Send them a screen shot, get the miles matched.

  17. AA distance based award were calculated by O&D mileage until SEP 2008. I flew 45K miles on oneworld carriers in F/J for 100K AA miles.

  18. Back in 1978, at the age of 24, I purchased a lifetime Red Carpet Club membership for $300.
    My parents thought I was crazy. Lived in HNL for about 4 years(1978-82) and my brother was stationed in the USAF. We used to go to the RCC and have drinks and pupus while watching the military jets taking off atfer work. Fun times.

    I continue to use the membership today and it’s been great when travelling both by myself on business, but also with my family.

    I believe it works out to about $7.50 per year..

  19. #2 seems low compared to the others. I used the eHarmony/ promo of ~140 Avios/$1 last year and tied it to the 25th Anniversary Iberia sale to book super cheap business class to Europe this Spring. But as good a deal as that was, it’s nothing compared to, say, MSing the Mint.

  20. Still available now. Start your trip in Marrakech, Marocco and travel to Johanesburgh SA on LUFTHANSA FIRST CLASS FOR 60K UNITED MILES. I bought my ticket last year and payed only 35k miles. Waited for the legs in first to open a week before departure and voila payed the extra 10k to jump into first for 45k miles. The FRA-JNB leg will easily go over 12k. At 45k miles you do the math…. if you start in europe the ticket cost goes to 100k so starting in north africa does the trick. Now it cost 60k still amazing if you ask me

  21. Slam Dunk: 1988 – Triple miles on all major airlines, applied even to minimum 1000 miles credits (Eastern) and before elite status credits.

    A 109-mile flight from TUS to PHX cost $14, earned 3000 miles, plus another 1000 with status.

    Hard to find a mileage run that did not pay for itself that year.

    The lucrative bonuses proved costly for the airlines, who began to find ways to diminish points values — a technique they have since mastered.

    For frequent flyers, 1988 was the “gold old days.”

  22. Triple EQM on AA a few years ago for certain flights. As low as $79 one-way ORD-SFO. You could pay with 20%-off AA GCs purchased at Costco. And 2% back with top membership.

    I think AA EXP obtained in January (and 33k AA miles for the actual base flights) worked out to cost as low as $1300 all-in. I met a guy who flew 3 straight days over a long weekend and had EXP by Jan. 7 and did not even miss any work.

    There were hundreds of us doing it. We even had a Flyertalk group for meetups in Admirals Clubs.

    Another very short-lived one was Citibank’s ill-fated competitor to PayPal called c2it. Email money to someone and charge it to your AA-earning credit card for no fee. Send $5k to your wife and have her send it back. 10k in 5 minutes, no cost. Hahahahaha

  23. There were several banks that offered deals similar to the old CITI TYP in 1995-2001. Started with Old Kent Bank’s CardMiles program – spend $20,000; get a domestic round trip ticket with no dollar cap. I regularly converted these into $1,500-$2,000 worth of travel on United. Legacy United also offered the ability to exchange for a lower value ticket in the name of the original traveler, then receive a voucher for the difference that could be used to pay for another person’s travel. There were several other similar programs – Zion Bank, TravelSmart, Webmiles, and I think one or two others.

  24. 2008 IHG and Hyatt: “2 Stays = 1 Free Night at Any Property Worldwide.” I would hotel hop from Holiday Inn Expresses for work. Redeemed for Intercontinental Paris and Intercontinental London for a week, each. Amazing redemption! I miss Marriott’s Gold/Platinum BOGO promotion at Renaissance and Marriotts. Saved thousands on leisure travel!

  25. Marriott’s current promotion. From your second stay on get an extra 2000 MR points (not SPG points)

    Just kidding…. I missed the above totally.

Leave a Reply

Your email address will not be published.