A title like that and this post isn't even about the North End or even Winnipeg!
I've mentioned before that I'm a bit of a fan of customer loyalty programs. I like to think that I am one of the small percentage that actually come out ahead. Although, if the rumoured changes come about that will allow merchants to tack on the cost of the Visa transaction to the consumer that might all change. They do that in Europe a lot but as far as I'm aware it is currently not allowed here in Canada. I have noticed though that discount airline Allegiant has started offering a discount for those that pay by debit rather than credit, so officially it's not an extra charge to pay by credit card, but it also won't allow you to get the rock bottom price.
Alright, so first to get some bragging out of the way and to lend some credibility to where I'm coming from. Over the years I have taken the following free* flights: First on Airmiles (the kind you get at Safeway and Shell): I have gotten 5 tickets to NYC, 4 to Las Vegas, and also gone to Newfoundland, Nova Scotia and Montreal. With Aeroplan (the Air Canada rewards program) I have gone to the UK, Nicaragua and business class to Argentina. I also still have enough Aeroplan points to take 8 flights within North America (or less flights to more far flung destinations, but I'm pretty sure I have enough to go anywhere in the world, twice).
Here are some very general tips and tricks that have served me the best (and later two awesome new promos that you should seriously consider). First, when it comes to Airmiles, the only way you'll ever get enough to leave your driveway is if you use the bonus offers that Safeway frequently has. Stock up on things you love. One of the best is the buy X boxes of cereal get XX bonus miles. Cereal keeps for ages and this promo also only happens when the cereal is on sale to begin with. Try to partner this with one of their "spend $100 get 100 (or sometimes even better, 250) bonus Airmiles events. Sometimes stores are having this as an unadvertised promotion. Let your fingers do the walking and call them first.
Also, with Airmiles, and this is a trick I haven't tried personally but have been told it works: when they have that coupon in the flyer chances are the "same" coupon got sent out in the weekly Safeway Club Card email. However, I'm told they tend to have different PLU numbers, so if you go the self checkout route you can self scan both coupons and get it twice. Worth a shot. The other big Airmiles trick is to know your zones. All of Ontario is considered one zone, so they presumably base their required amount of miles on a Toronto departure - as a Winnipegger, if you are wanting to redeem for a few people it is well worth the drive to depart from Thunder Bay instead. To put this in perspective, from Winnipeg to NYC in high season you would need 2950 Airmiles per person. From Thunder Bay? 1400. Less than half. The gas for the 8 hour drive pays for itself even with one person but definitely worth it for 2 or more. Have the BMO Airmiles Mastercard? You'll need even fewer.
Now, on to Aeroplan, my favourite program.
I pay the $120/yr for my Visa card. I know many people who say they would never pay for their credit card, but for me it's well worth it. Most premium credit cards, mine being the CIBC Infinite Aerogold Card, offer various bonus coverage - read the fine print to compare. I get up to 2 weeks at a time of travel health coverage, baggage insurance, purchase protection and others. The feature I use the most is probably the CDW (Collision Damage Waiver) insurance for rental cars. I once curbed a rental car and the rental place wanted to charge me $175 for the scuff on the rim; my card covered it for me. The other ones? Well, I haven't used them yet, but like any insurance, you hope to never need to. I print out their little brochures and take them with me when I travel so I have it handy for what I'm covered for. With some of the trip coverage if my flight ever gets delayed by XX hours (I don't remember exactly how many) they will even cover entertainment expenses!
I also pay my credit card off in full every month, the only reason I use it is just to get the points. And boy oh boy, am I obsessive about the points. About the only thing I don't put on the card are garage sale shopping and my Hydro bill (because stupid Hydro won't take Visa). So, every year, based on my spending, I earn at least one free* flight within North America. You could even argue it isn't free because I paid $120 for the card. Fine, I can fly to anywhere in the continental US/Canada for $120 plus the "*". What is the * you ask? Well, if you've ever redeemed for a "free" flight you'll know that you still get dinged for the taxes and fees, I find usually $100-200 for a North American flight. Pro tip on how to keep that number low? If you are flying to Europe, route yourself through the States, the taxes and fees are much less.
Okay, so other tips and tricks for Aeroplan. First, definitely if doing online shopping sign in to their eStore first (via the Aeroplan homepage). They often run promotions like 5 or 10x the Aeroplan purchases. If it's something you just want eventually and don't need it p.d.q. then wait and buy it during the promo. You could potentially earn 1000's of bonus miles. I once bought something off eBay during a 10x the point event and got 4,000 bonus points! Pro tip: they changed how you accumulate using eBay and you no longer get points for things in your "watch list", be sure to unwatch the item before you bid.
Second, using the CIBC Aerogold as an example, pre-pay for things you buy by buying gift cards at supermarkets. The CIBC Aerogold card gives you 1.5x the points at grocery stores. So, if I know I'm about to go drop a few hundred bucks at Home Depot, I stop at Safeway first and buy the gift cards there.
Here's my new thing: Visa and Safeway are having a promotion in November that every time you spend $200 in a single transaction you will get a $20 credit back on your Visa, up to 4 credits or $80. You just need to register your card. I've read the fine print and it doesn't seem to say that this isn't applicable on the purchase of gift cards; so if you're like me and you maybe buy $200 of groceries in the entire month, worry not, just stock up on gift cards either for yourself for future purchases or for unimaginative Christmas gifts! If I stockpile Home Depot cards it would be like getting $800 worth of stuff for $720 and I would get 1200 points instead of $800.
Second awesome promotion I came across the other day: Get a fancypants Amex. Yes, the yearly fee in mindblowing ($499!) but do the math. For $499 you get 50,000 Aeroplan points. That is enough for two round trip tickets within North America. Even by the time you pay the taxes and fees on your tickets you are still flying anywhere you want for less than about $350pp. On that flight the cardholder gets access to the Air Canada lounges, where being the good Winnipegger that they are, if they are flying with a friend they will go in and stock up on free food to their friend waiting in the regular part of the airport. Other options? Well, with this Amex you get one free short-haul (from Winnipeg this basically means to Toronto/Ottawa/Regina/Saskatoon/Minneapolis) companion ticket. So, you redeem 15,000 of your 50,000 points, you and a friend go to the center of the universe for a weekend getaway and you still have 35,000 points left - enough to go anywhere in North America or, if you wait until you've got another 5,000 points ($4000 of spending if you don't get any bonuses) you can go to Mexico, the Caribbean or Central America. Cancel the card when it comes up for renewal next year.