Count Me In! The Miles and Points Plays That Got Me, For Better or Worse

This post may contain affiliate links; please read our advertiser disclosure for more information.

Best Points and Miles

You Got Me!  The Best Points and Miles Plays That Sucked Me In

I’m increasingly selective with the points and miles promotions I pursue.  But looking back, I’ve willingly gone after many silly promotions.  Some have worked out great, others just ok, and a few not at all.  That’s all fine, though, because I feel I have come out ahead over the long term.  Like much in this hobby, I look back at each individual play and enjoy it for what it is or was.  At bare minimum, at least I have a good story!  Here are the best points and miles plays I’ve fallen for over the years.

JetBlue Virgin America Points Match

About five years ago, JetBlue offered 75k TrueBlue points to anyone with a certain Virgin America mileage balance who also took any round trip on JetBlue.  It just so happened that I had a healthy Virgin America mileage balance (thanks, Amex), and I decided to take JetBlue up on the challenge.  I took a short round trip to Hartford in order to qualify for the offer.  Yes, I allowed JetBlue to alter my travel behavior for this trip.  But I love the Northeast, hadn’t yet explored the Hartford area, and wanted to hit a few joints George Motz recommended, anyway.

Long story short, I left early on a Saturday and returned that same night.  Note to self, the rental car counters at the Hartford airport can be painfully slow.  I ended up turning the 75k TrueBlue points into 37.5k Amtrak points.  That’s over $1k in point value!

Best Points and Miles

IHG Points Breaks

Points Breaks, how I miss you so.  The 5k version was the best – I never bothered with the tiered 5k/10k/15k version.  IHG directly affected my travel behavior by offering select hotels at 5k points per night.  A few times each year, I experienced the joy of the new Points Breaks list.  Some were hits, others misses.  But it was always fun.  Oddly enough, I think all of my Points Breaks redemptions were for Holiday Inn Express properties.  Perhaps that was purely due to my cinnamon roll weakness.  But, alas, Points Breaks is long gone, as is most any high value redemption with IHG points.  Pour one out.

Restaurant Portal Rewards

Years ago, I spent more time than I care to admit searching airline and hotel dining portals for restaurants worthy of visiting for easy points and miles.  Each and every time, I came up empty.  Sure, maybe I didn’t lose here, since I never fell for it.  Regardless, I blew hours on these searches.  I have my wife to thank for a groundbreaking realization:

“If a restaurant has to resort to providing bonus points or miles to bring in customers, the food probably isn’t good, anyway.”

I should have listened to her from the beginning.

Best Points and Miles
Just one example of an airline portal promotion.

Airline Portals

Over the years, I’ve rationalized unnecessary shopping trips thanks to bonus airline shopping portal promotions.  Sure, we consumed everything we purchased, but I admit that these portals influenced my behavior.  In the years since, I’ve found ways to meet the bonus thresholds in other ways, primarily thought  Nonetheless, I must admit that the portals nailed me early on.

“Stay” Mattress Runs

While I never have taken a specific trip solely to earn elite status, I do recall jumping hotels on certain trips to increase my stay count for status.  I equally remember the death stares from my wife for having to unnecessarily move hotels.  Sure, I may have ended up the hero when the elite status paid off (hello, Napua Tower at the Grand Wailea).  But those occasions paled in comparison to the ridiculous hotel changes.  Never again.

Best Points and Miles

Bonus Fuel Points – One of the Easiest, Best Points and Miles Plays

I still fall for this one.  Kroger, the supermarket chain that gets most of my fuel points attention, periodically offers bonus fuel points on gift card purchases.  Yes, the 4x promos happen often, but I’m particularly susceptible to the bonus 200 points promos.  Specifically, certain third party gift cards earn 200 bonus points on top of the 4x points.  Not coincidentally, I’ll convince myself that I need more Domino’s Pizza or Happy gift cards in my life.  I can’t be alone here.

Delivery Service Credits

This one is relatively new on the scene, but it’s a growing issue for me.  With more Amex cards come many more Uber Eats and GrubHub credits.  We are increasingly in a situation where there aren’t enough meals in the month to consume them all.  I know, this is a good problem.  Regardless, for the sake of consuming all of the credits, we do so in a less than economical fashion.  Specifically, we “pay” close to twice as much for options than we would normally.  We are resisting this by making fewer monthly orders and more generously tipping some of the most underappreciated workers out there, delivery drivers.  Regardless, we settle for overpriced food due to these credits.

Best Points and Miles Plays – Conclusion

These are just a few of the best points and miles-related plays I’ve fallen for over the years.  There will be more, and that’s fine with me.  Some may get the best of me, and others may open my mind to plays I wouldn’t have considered otherwise.  Over the long haul, we end up ahead.  Beyond any one play, I’m continually enthralled by the evolution and creativity of points and miles promotions.  I feel it just keeps getting better.  What about you?

Benjy Harmon
Benjy is a fan of points, miles, and financial independence (FI). An experienced world traveler, husband, and father, he currently focuses on roaming throughout the USA expense-free (or close to it). He enjoys helping others achieve their FI and travel goals.

More Like This


Responses are not provided or commissioned by the bank advertiser. Responses have not been reviewed, approved or otherwise endorsed by the bank advertiser. It is not the bank advertiser's responsibility to ensure all posts and/or questions are answered.


  1. Having just started this “game” two years before Covid shut everything down, I’m done chasing useless points in useless rewards programs! Got 5 new credit cards before my month long trip to California and worked strategically on that trip to make all the spend to get ALL those bonus points, only to not be able to use them last year and for the immediate future. And Choice Privileges nailed the coffin shut when they took my 90,000 points because I didn’t realize they were expiring Dec 31st due to no traveling last year. Wyndham reinstated my points (which expired recently as well) when I asked, but Choice wouldn’t budge, stating they make no exceptions for any reason, not even pandemics apparently. I’m sitting on so many Hilton, Hyatt, Marriott, SWA points and reward certs that it’s creating more stress (worrying about upcoming free night certificate expiration dates) than it’s worth. I would never recommend to any family or friends to bother with all this nonsense. Having Covid last year taught me that Life’s too short for so much aggravation. (Reminds me why nobody clips coupons anymore)! And now seeing how ludicrously many points (vs cash price of rooms lately) I need for IHG and Hilton, just makes me sick to my stomach. These loyalty programs devaluing their programs so greatly in just the last few years have sucked the joy out of travel for me. Maybe it’s just bad timing on my part? Or maybe just the beginning of the end as we all get burnt badly by the travel industry and bank credit cards? All this in such a short span of time has left a very bad taste in my mouth and I won’t ever forget losing those points to Choice Privileges, it is seared in my brain. So, I caution everyone to think VERY hard on whether any of these credit card or rewards programs are worth it anymore going forward. Travel has been irreparably changed this past year, at least for me.

  2. While I greatly admire your optimism I really don’t see promotions getting better. I like Kroger fuel points a lot but often accrue more than I can use. IHG Points Breaks was truly amazing at 5,000 points and the index card promotion was great but it’s been quite some time since they had anything decent. Mileage and/or mattress running has certainly seen better days. I’m not saying that promotions are terrible, just worse than they were.

    • Christian,

      I can understand that take. My “getting better” comment has more to do with the changing creativity and scope of promotions. Certainly, many promotions were perhaps more lucrative before than now. Indeed, despite that, I try to be optimistic.

  3. My favorite was the 2005 AirTran “32 Wendy’s cups for a free flight” promotion. I remember meeting a dirty dumpster diver-type in a parking lot somewhere to buy hundreds of Wendy’s cups off of Craigslist. Everyone got free airline tickets that Christmas!


Please enter your comment!
Please enter your name here


RebatesMe - $40 Bonus!

Super easy bonus! Sign-up and they'll pay you $40 after your earn $10 cashback. That's it!
Grab Your RebatesMe Bonus!

Webull - 2 Free Stocks!

Brokerage app Webull is offering 2 Free Stocks! Just open an account and fund with $100 to get your stocks valued up to $1600! Super easy!
Grab your 2 free stocks now!

Subscribe To Our Newsletter

Join thousands of MtM readers who are subscribed to receive a once daily email with all of our posts. Never miss out!

You have Successfully Subscribed!