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This is my journey to get myself 16,500 free Aeroplan points. It took a while, but in the end I was able to take a mini vacation!

Back in May, my buddy Saving Mentor posted a fantastic “heads up” post on the Aeroplan Star Challenge, where you could earn 16,500 points basically free.

For those of you who aren’t familiar with Aeroplan, they are a points program where you can get free flights for Air Canada as long as you have a minimum number of points.  You can also get merchandise or other paraphernalia, but I would much rather get flights.

16,500 points is the typical number of points you would get if you signed up for a Aeroplan credit card, usually with an annual fee (e.g. $129 per year for an Aeroplan points card).  16,500 points gets you a free return short haul flight.  If you have 25,000 Aeroplan points, you can go anywhere in North America on Aeroplan!

The task to get the Aeroplan points was to collect 70 points.  One of the easiest ways to do this was to go to Esso (a participating Aeroplan partner in the challenge).  Each transaction is worth 2 points.  Therefore, if I got 35 transactions in the specified time period (28 days), I would have reached the 70 points, and thus the 16,500 Aeroplan points.

Of course, this got me excited.

You’re probably wondering… how does one get 35 transactions with Esso?  Well, not through $45 fill ups at the gas station.  If I only fill up every 10 days on average, that’s a measly 6 points.  Not enough to score the 16,500 Aeroplan points of course.

Confessions of a Points Addict

So what did I end up doing?

I scoured over Red Flag Deals (where other points addicts unite) and followed Saving Mentor’s suggestion for frequent transactions at Esso.  Every $3 at Esso gives you 1 Aeroplan point.

Yes, you guessed it right.  I ended up going to Esso, and did 3-5 transactions of $3 each time I went to get gas (I think I went about 6 to 10 times and did 3-5 transactions), I went to Home Hardware once for one transaction, and exchanged points on Points.com for a few points.

All these mini-transactions were legit and Aeroplan nor Esso had no issues with this, according to the rules and regulations of the points challenge.

The Low Point

I went to gas up at night usually, and actually felt adrenaline rushing through me as I made my $3 transaction.  Then inserted the ol’ credit card for another $3 transaction.  Then inserted my debit card for another $3 transaction.  I felt like a points junkie.  I would peer over the gas bar to see if the attendant was looking at me from the safety of his glass window.  If I didn’t see any eye contact or suspicion, I would go ahead and try for another $3 transaction.  I would peer again.

Early on in my Esso escapades, one of the gas station attendents came out, furious looking.  He said to me “Stop it with the $3 transactions!  Why three dollars? Why? Why is everyone doing this?”

My only reply was: “Other people are doing this?”

Suddenly, I didn’t feel so alone.  The Red Flag Deal effect was on.  Everyone else was doing the same thing.

The other low point was when the credit card became suspicious of the frequent, numerous transactions at Esso.  They called me and I explained that everything was fine, it was just me who was doing the frequent transactions.  I knew that this would happen (which is a good thing because that means that the security fraud protection team from the credit card company was actually doing their job) and this didn’t give me the same adrenaline rush as pumping gasoline at $3 each time did.

The Payoff…

After all that work (it was a lot of work), I was anxious to see whether it would pay off.  Like many others on Red Flag Deals, I was waiting for the congratulatory email that said “Congratulations!  You have earned 16,500 Aeroplan points!”

After a few weeks, that wonderful email came.

The payoff came when, after taking eons to earn Aeroplan points, I get a whopping 16,500 Aeroplan points credited to my Aeroplan account.  Then I was able to use it for a short haul flight and a mini-getaway with my boyfriend.  I saved over $200 (still had to pay about $70 of taxes and fuel surcharges and other yucky expenses for the free ticket).

In the end, I would do it again!  It was a lot of work but also a lot of pay off.  There you have it folks, I am a points junkie and I’m not afraid to admit it.

Readers, how far have you gone to score a deal?  What are your confessions?

Article comments


I’m amused and disturbed at the same time. 🙂

Young says:

@Marissa- lol isn’t it sad? … I just like a good deal. Maybe I should start a local chapter of “Desperate Deals Anonymous”

Haha…nice! I’ve done things like this before, but not really anything that had such a huge pay-off. I’m cracking up about the $1 coins, too. I can totally see myself doing something like this. Hope you and the BF have a great time!

young says:

@ff- lol a girl’s gotta do what a frugal girls’ gotta do!! 🙂 We did have a lovely time, thank you! It was well worth the indignity, IMO

SavingMentor says:

Thanks for the mention – I was so happy to hear that you got the points just like I did. I too did the Esso thing but I think I did more like 15 transactions at a time though right when my gas tank was on empty. I did it for both my wife’s account and my account so we got 33,000 points total. I did have a gas station attendant stop me once, but fortunately my tank become full right when he came out to stop me. I did most of the transactions at the same gas station.

I bought Esso gift cards in advance like someone on RFD mentioned to avoid the problems with my credit card. Definitely worth the trouble. 25,000 of those points will be used for a roughly $700 ticket to Vancouver from the Maritimes for me.

young says:

@SM- Wow, 15 transactions! I think my tank is small- 35 L so I couldn’t do that many and I was scared they would come out. I did go to several different Esso gas stations on the same night lol. It’s nice when you live in a big city to be able to do that.

Nice- congrats on the free ticket from YVR to maritimes! I wish I could motivate my BF to do it but he’s too dignified to do something like that. haha. He was proud that I was able t get 16,500 points though!

SavingMentor says:

Well, I didn’t really convince her. I just “borrowed” her Aeroplan card as well as her car and did it all for her. She’s one lucky girl. I do all the work and she usually gets to partake in the rewards 🙂

Young says:

@SavingMentor- LOL! She IS one lucky girl! All frugal and extremist partners are lucky to be in a relationship with us frugal extremists lol.

Have never really gone to any extreme measures – yet! But now that I finally have a cash rewards credit card, I’ve been thinking of all the ways to spend more $ on it to get the points!

young says:

@Pamela- Is it the MBNA Smart Cash card? 🙂 Yes.. once you get addicted to rewards cards, you won’t be able to go back.

Chris H says:

I took the more risky approach for the aeroplan points challange. I did the points.com exchange 25 times from esso points to aeroplan 1 point at a time. Did this for my entire family 5+ people and over 10 friends, everyone got creditied the 16.5k points no problems. Took about an hour of time and I earned for everyone a combined value of over 3k. I’ve since flown to vancouver and my family has taken trips overseas as the points boosted them to the threshold they needed.

SavingMentor says:

I would have done that as well as it was definitely the easiest way but Points.com shut it down very quickly so it didn’t work anymore after 24-48 hours I think. Those who got in on that method definitely didn’t have to spend much time getting the needed number of transactions. Definitely an even sweeter deal!

young says:

@Chris- Yeah, I read about that and was tempted, but I was too worried that it wouldn’t work. Great to hear that it worked for you!! You got to get your 16,500 points without the shame and embarassment that I experienced lol.

Hmmm, I don’t think I’ve ever gone to that kind of an effort to score a deal, but back when I used to have cable (as a student) I got into some shenanigans with my fianc

Teacher Man says:

Now that’s just smart buddy. Cheers!

young says:

@Jordann- I concur with TM- that sounds very good… and smart!

BeachBoy says:

and you’re telling us that AFTER the deal is over???

I mean it’s cool for you but I would’ve like dot get that deal too!!! I use my card almost every day, but it’s not enough to get 35 transactions per month

young says:

@BeachBoy- lol sorry man! You should check out Saving Mentor’s page- he’s pretty good at updating about deals. I didn’t want to post about it because I was worried that I wouldn’t get the points.. and then angry readers would be after me! 🙂

Jennifer says:

It depends on how desperate you are as to how far you will go. I did something similarly crazy a few years ago to get a $500 gift card. it was ridiculous the hoops I had to jump through, ,but they worked and in the end I had spent about $100 and 5 hours of time to get the $500 gift card. We really needed the money, so it was worth it, but I seriously questioned my sanity at the time.

young says:

@Jennifer- A net $400 for five hours of time. I would definitely do the same thing especially if it was guaranteed. Haha, sometimes when your’e in the middle of it all, it’s easy to get carried away. I certainly did not think I was irrational when I was busy getting my Aeroplan points .

Rob says:

Me, not much living over here in Europe we don’t really have anything that good. But the best deal I ever saw was people who ordered dollar coins (crazy Americans don’t like loonies) like $25,000 worth from the mint on their gold miles card and then turn around and deposit the whole bit back into the bank, rinse wash repeat.

young says:

@Rob- Haha wow that sounds like a smart idea! I would have probably done the same and I thnk that’s a lot of money for not too much trouble.