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The Beginning of the Points & Miles Journey

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Like many, I’ve been slowly accumulating my Alaska Airlines and Delta miles over the years and cashing them in for award flights every now and then.

But a conversation with a colleague prompted me to take a harder look into the points and miles game as she divulged the astounding number of miles she had accumulated by pairing her (albeit business class) work travel with the Amex Delta Platinum card.

I was transfixed as she explained how she charged all her meals at the hotel to her room, taking advantage of the 3X benefits for hotel charges instead of merely getting the 2X points she would have received by paying with her card at the restaurant.

And so my obsession began. And the more I learned, the more I realized how much I’d been missing out on all these years.

In the 2 years since I embarked on this journey of strategizing my spending and points chasing, I’ve already made numerous mistakes and learned an incredible amount of useful information from myriad points chasers that have come before me.  Their blogs, newsletters and Instagram accounts have taught millions of travelers and everyday people the ins and outs of maximizing your dollar and reworking the way we think about spending and making the capitalistic system work for us.   

If we are already spending money on groceries, gas and dining out, why the hell shouldn’t we get something a little extra in return?

After excitedly applying for, and getting approved, for the Delta Platinum Amex myself, I realized that I had missed an opportunity to boost my husband’s American Express points stash had he sent me a referral code as he was already an Amex holder. 

Mistake Number One.  

My continued research also showed me that there were much better options for travel cards on the market as I was now siloed strictly in Delta miles. Delta, admittedly a very comfortable and punctual ride, is notorious for above average award prices for flights, so I was doing myself no favors if cheap flights was my ultimate goal, which it was.

Additionally, the card did not offer other benefits such as complimentary lounge access as many other cards in the mid-tier travel cards range included.  Sure, the card awarded a free checked bag and a free annual companion fare, but Delta flights were far more expensive than many other carriers and I was already getting a free checked bag because I was Silver medallion status.

That was Mistake Number Two.

sad dog

At the time, this card’s annual fee was $250.  It has since risen to $350, and as someone who lives in Portland, Oregon, getting the Alaska Airlines card, which also awards an annual companion fare and a free checked bag and clocks in at $95 a year, the Delta Amex card felt less and less desirable. I had let my impulsivity get the best of me and I quickly had some point chasing regrets.

To be fair, the Alaska cards multipliers are not great either- spending on the card awards only 3X for money spent on Alaska tickets and 2X for things like gas and EV charging, but everything else only awards a mile per dollar. And as any point-chaser will tell you, you should never get anything less than 2 points per mile on any purchase.   

Months later I discovered that booking hotels through Alaska’s website was actually some of the hidden magic of the card. 

Using Alaska airlines hotel portal, you could earn thousands of miles per booking. However, shortly after this discovery, Alaska Airlines partnered with Expedia and has since significantly devalued the miles earnings, which are now abysmal at a few hundred per booking. 

For hotel bookings I now recommend using a third party portal such as Rocketmiles.com, or utilizing the credit card travel portals for Capital One, Chase, or American Express, which offer mileage multipliers on hotel or vacation home bookings. The exact multiplier will depend on the credit card, but they they can be a huge boost to your points cache. Credit card loyalty programs also have shopping portals which offer multipliers for brands like Booking.com, Priceline.com, or vacation rental agencies like Airbnb and VRBO.

Despite its low multipliers, I keep the Alaska card as I love the free checked bag, especially with rising checked bag costs that abound. I also look forward to the companion fare each year as it comes in really handy during peak travel times. I specify ‘peak travel times’ as like Delta, Alaska flights tend to be a bit pricier and often I am able to find cheaper flights elsewhere except during holidays when Alaska’s buddy pass ends up being the better deal.

Final Thoughts

I’ve been through a few iterations of credit card ownership with the intent of points chasing in just a few short years, and there is always more to learn as the landscape is changing constantly. As someone as frugal and planning-oriented as I am, it’s unconscionable that I came so late to the points and miles game. With the right strategy and patience, the payoff can be huge and has helped me achieve traveling a way that did not think was possible.

While I agree that the entire system of credit cards has its own issues, such as its role in increasing prices to offset the points awards or that the credit system itself can be downright predatory and discriminatory, I also understand that it is a far larger issue within our Capitalistic society, and that disliking the financial system and its current format does not do anything to change it.

Thus, I will play the game because it is helping me travel more, simply by spending money that was already being spent to live my life. The gamification of it has also been helpful for me psychologically. Getting something in return for the cost of dental bills, groceries, pet food and the utilities- it softens the blow of the ever-increasing costs of just plain existing.

So I will continue partake, putting stickers on my credit cards to remember which card is for dining and which one is for groceries, utilize shopping portals as much as I can, and spend my way towards my next trip because that at least is something that I can control.

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