What’s the craziest thing you’ve done for miles? Read the winning entries here!

Think you've done crazy things for miles? Check out these stories...

Over the past week, The Milelion has been running a giveaway in conjunction with OCBC to mark the launch of the OCBC 90°N Card. The question was:

“Tell me your craziest miles story”

We got 40 different answers, and it was really hard because there were so many incredible stories to choose from. Nonetheless, I’ve picked my 10 favourites, who have each won a $50 Takashimaya Voucher. I’ll be contacting you via email, so keep an eye out!

So here goes…the 10 craziest miles stories, courtesy of the Milelion Community.

Miles chasing is a family business, and it helps if everyone’s on the same page. So what if it means asking them to delay a vacation? MSS doesn’t see anything wrong…

Nerve wrecking moment during the SCB X fiasco, forced my bro and sis in law to postpone their flight tix purchased for a few days and ‘invested’ in the holding fee out of my own pocket. They were confused and amused when i tried persuading them to delay. only crazy miles gamer would do that.

Speaking of family, there’s no reason not to get the little ones involved. These are after all important life skills, as Rili can attest to…

The day I learnt of the miles game,I sat my family down and spent half a day explaining the intricacies of using the various supp cards to optimise for miles. Even gave my kids a pop quiz when I brought my kids to the toy shop. When I asked which card to use for the pay wave transaction, the little one whipped out the PPV card. I’m so proud

That said, there are right ways and wrong ways of involving the little ones. Wayne’s probably sleeping on the couch for the foreseeable future…

I once went for a deliberate holiday to make full use of expiring miles, wife and 11mth old infant in tow. Detoured SIN – TPE – Okinawa instead of flying direct to experience SQ regional 787 J. Entire journey took us close to 15 hours from home to hotel with a fussy baby the whole way. That night, my wife told me to stop my miles chasing nonsense. To top it all off, Sq swapped equipment on us and we sat the old regional J on the A330 instead of the 787!

Perhaps he could make it up to the wifey by taking a leaf from lifeonthego_k’s book. Want to show her the good life without paying through the nose? Why not treat her to a relaxing day of fine food, fine wine, massage therapy, and a romantic spa cabana, all on the airline’s dime? Just be prepared to explain it to the check-in staff…

I was a One World Emerald member and had Asia Miles expiring, but just enough for 2 one way tickets in Y with CX from HK to SIN. Luckily, it was also my Fiancé’s birthday and I conjured up a plan that she would def. remember for years to come. So what did I do? Well, she didn’t have any vacation left, so I bought a cheap one-way tickets for the Saturday morning after her birthday (which fell during the work week) from SIN to HKG with Jetstar and redeemed tickets with CX in Y for the same day evening back to SIN. This would give us the better part of the day to relax at Cathay’s spectacular First Class lounges in HK – champagne lunch, complementary massage, a cabana – the works! At Changi my plans were almost scuttled as the Jetstar staff refused to check me in as I didn’t have the necessary Visa authorization to enter HK (which is required for Indian passport holders). But after pleading with the Jetstar check-in staff, showing their manager my boarding pass for the same day return, promising I won’t try entering HK and taking in bemused looks from all their staff as to why the hell I was going to HK just to stay at the airport and use the lounge, they allowed me to board! We had a fantastic time and were back in Singapore just in time for a nightcap

That may sound crazy, but really, with all the shenanigans that miles chasers get up to, it’s amazing some of us haven’t been put on no-fly lists. Dizzy may want to watch his back the next time he visits Fortress America…

Flew to SFO for a quick turn mileage run and got questioned by CBP for purpose of visit and duration of stay which was 5 hours. Flew back for the second mileage run in 2 days and met the same CBP officer and gave the same answer, to which she replied, “Don’t do this again!”

You won’t need to do mileage runs for a while if you snag yourself a 100,000 miles sign up bonus. That’s what the SCB X Card has on offer, but many people are having difficulty spending $6,000 in 60 days. Fortunately, Jia Min has an idea…

When the x card first came out, due to the 6k spend required to get the 100k miles, a colleague of mine set up an auction floor to see who will give him the greatest discount(cashback) to pay 6k for his wedding banquet

Pop quiz. What’s the biggest discount you should be willing to offer on this $6,000 payment? If you value your miles at 1.8 cents each, the answer is $1,104.50 (remember you’re paying $695.50 for the annual fee, with 100,000 miles on the line). An 18% discount, courtesy of your office’s friendly miles chaser.

Indeed, miles chasers can be a very helpful and agreeable bunch. We’ll help you buy lunch! We’ll call the Grab for the client meeting! We’ll volunteer to source and buy the gifts for the office dinner and dance! (just make sure we get reimbursed).

Chs takes that one level further…

I voluntarily helped a non-tech-savy client upgrade all the computers in his office and set up all his new laptops, including installing printer drivers, office, anti-virus etc. so that I could earn miles for all the computer purchases. I’m still the default IT help desk support for him now more than a year later…

IT support aside, miles chasers will also gladly help train frontline staff in the use of contactless payment technologies. Samsung owes a debt of gratitude to Milecub no 2…

I religiously borrowed a Samsung Gear 3 from a friend several times so that I can pay hospital bills via MST with OCBC TR during the 4mpd mobile payments period. The cashier was perplexed when she asked me for my credit card during payment, and I said to just enter the payment amount into the terminal. She almost didn’t let me tap my watch, and had to get her supervisor involved – I had to explain to them how MST works, tapped the watch against their payment terminal under their watchful eyes, and get to witness the look of disbelief on their faces. Ah, the magic of technology, and the desperate lengths we go for 4mpd.

From desperate lengths to desperate heights- remember Mileslife Health? I’m sure some people rushed out to buy a phone shaker gizmo, but Zee’s determined to earn his miles the good honest way…

Back in the day when Mileslife was still in existence, I actually climbed 12 stories at work everyday to clock my ‘mileage’ (literally) for Mileslife health. Till this day my wife is still unwilling to come by my office for fear of the office lift breaking down; which was my excuse then for my Mileslife mileage run!

Zee may be burning calories, but other people are loading them on. Chope’s recently imposed a cap on the maximum number of KrisFlyer miles users can redeem each month. Good thing See Hong made hay while he could…

In 2018, when Chope was still able to redeem more than 1K miles per month, I made about 235 Chope reservations for that year alone. I tried my best to spend between $3 to $8 for each reservation by searching for the restaurants/cafes with no minimum spend with cheap drinks and/or food, many times having a meal in a place, a drink in another and dessert in the third one, amassing promo codes through the Chope birthday promo, angbao promo, liveup trial etc. Total Chope$ went to about 100K and converted to about 80K KrisFlyer miles. This is just from Chope, there were times where I was able to double dip with Mileslife and others. It was also back then, I was explaining to my then-friend, now-girlfriend about how all these work and she started joining me in the game.


Congratulations once again to the 10 winners, and be sure to check out all the answers in the comments section of this post. I can’t wait to see what crazy stories the next big miles promo throws up.

(Cover photo: come on, you know who this is right?)

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Aaron Wong
Aaron Wong
Aaron founded The Milelion to help people travel better for less and impress chiobu. He was 50% successful.

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The craziest thing I did: I love miles so much I even wrote a blog detailing my experiences and until now, I haven’t even earned a single cent from it! If that is not passion, I don’t know what is!

KM Tiger

Your blog is utter rubbish. You claimed that each mile is worth 5 cents and the only SCB X transfer partner you know is KF. It’s no wonder nobody reads your blog.

Karl Fortune

It used to be good, but it now seems an avid critic can turn advocate quite quickly – it does seem companies can buy their love these days. Amex any one?


congrats for the winners~ for the unenlightened, who is the guy on the cover page?


man, im jealous now


didn’t know there was a deadline to the contest but still like to share my journey anyway because of something Louis wrote i thought worth sharing for those who didn’t come across that particular article was a one card cashback person previously because frankly, it’s oh so very convenient came across the milelion in early 2018 and was attracted by the contents even though i didn’t think the miles game was suitable for me since i didn’t have time to fly much, because it showed how much the banks could be giving back to me but i was settling for… Read more »


thanks Aaron, totally crazy typing that out at 4am while drowsy on painkillers but thinking miles makes me happy lol looking to learn more on hotel loyalty programs next when I have time to travel but from reading on that through the various blogs, I still find it incredulous the extent people goes to maintain more than one hotel loyalty program when the benefits seems to at most equate the measures they go to to keep a status, quantitatively in terms of net financial output at least only makes sense to me if they’re frequently on the road because of… Read more »



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