The Miles and Points Ghost of Christmas Past

Well, now that you have all opened your gifts, I come bearing the worst one of all. I’m here to remind you of all the miles you could have earned on those expensive Christmas purchases but didn’t. Brace for impact.

Yes, the Holidays are stressful and expensive. But no one said there isn’t an opportunity to reward oneself with a pile of bonus miles and possibly cashback even on those gifts that aren’t for yourself.

I have been known to return gifts I received for Christmas only to turn back around and re-purchase them, all so that I could take advantage of a promo or just using a portal. I loved hearing on NowBoarding’s podcast that Angelina from Angelina Travels does the same thing. Finally vindicated!

So what miles, you ask, have I left on the table this Holiday season? Here are a few:

Choosing the Right Card

Not all cards are created equal, just like their benefits certainly aren’t. Your Chase Freedom card bonus categories during Christmas was anything you paid with Chase Pay, Wholesale Clubs and Department stores, so that’s where you should have bought your kids toys this year.

The American Express Gold card (read more here) gives 4x for dining and 4x at supermarkets. All the food you bought for Christmas dinner and all the times you went out for brunch and mimosas to cope with the holiday stress should have gone into this card instead.

All of your gas expenses, or flights and hotels to visit your family for the holidays should have been paid with something like the Wells Fargo Propel card. You would have wound up with 3x points on those categories.

Now, obviously I don’t expect everyone to have 20 something credit cards like we do. But if you do have more than one, you should be always thinking about which one gives you the most for what you’re spending.

Too many cards?

Shopping Portals

Everyone loves shopping online. I know I do, particularly so that I don’t have to interact with other people or stand in annoying lines. But like with everything I do, I try to maximize my earnings as much as possible, and that’s why shopping portals play an important part in my retail experience.

The premise is quite simple.  Instead of going directly to the store’s website you would like to buy from, you first go to a portal. It then re-directs you to the store’s website.  Just by clicking through the portal, you’ll earn a certain number of miles for that purchase, usually 1-3x, but sometimes going upwards of 15-20x the purchase if there are any juicy promotions going on.

Alaska Airlines Shopping Portal

Alaska Airlines Shopping Portal

For example.  You’ve been jonesing for a new pair of Bose Quiet Comfort headphones that you want to buy at Best Buy.  Their website lists them for $299.99.  If you go to Best and make the purchase you’ll earn 300 miles from your credit card spending, BUT, if you go through Alaska Airlines’ Mileage Plan Shopping Portal FIRST, you’ll earn 2x the miles if you buy them from Bose directly.

2x $299.99 = 598 miles 

1x $299.99 = 300 miles from your credit card

Total = 898 miles for the headphones you wanted in the first place.  Not a bad deal!

One of the sites that I use for figuring out who has the best deals for shopping portals is, it will list the airline’s current offer for their portal.  Also, if you subscribe to the portal’s weekly email, you’ll get the bonus offers sent to you.  

Dining Programs

If you opted to dine out instead of staying home and cooking for Christmas, did you make sure you were getting extra miles for that? Many restaurants in most cities have joined airline dining programs in the hope that it will get you to come to their establishments.  Most if not all airlines participate in a program to allow you to earn miles for simply picking up the tab.  And when you do pay, the meal, drinks, tip, and tax is all included in the miles that you earn.  

All you have to do is add your credit card number into the system when you sign up.  Usually a week to ten days after you’ve paid the bill, the miles will be added to your account.  Simple and easy.

Yes, you’re right. You won’t be getting thousands of extra miles (unless your restaurant tab is about 10 times what mine usually are). But it all adds up, and it can definitely help top off certain account balances, or help keep those miles alive in programs with set expiration after inactivity. 

Skymiles Dining

Skymiles Dining

So if you do invite your extended family for Christmas dinner at one of the participating restaurants, make sure to offer to run your credit card and get everyone to give you cash. You’ll rack up a ton of miles that honestly aunt Susie will never take advantage of, or that cousin Bob will leave on the table when he uses his debit card to pay. This will more than make up for all of those socks you got for Christmas in years past. And you bet I’m making that dinner reservation through OpenTable so I also get points there.

Cash Back

If you instead agree with me that sometimes cash is king, you can instead use cash back credit cards, which allow you to get some percentage of the money you spent back on your statement. For example, the Capital One Savor card (read more here) will give you 4% back on anything you spend on the dining category. Another cash back option is the Capital One Quicksilver Cash Rewards (read more here), which gives you unlimited 1.5% on anything you spend every day.

Alternatively, you can use a cash back portal like TopCashBack in lieu of your airline portal if you prefer to get cash back instead of additional airline miles. If you’re a big spender, this will help you offset some of those expenses.

Credit Card Offers

Do make use of your Amex or Chase offers. Check your accounts regularly to see whether any of the purchases you intend to make would benefit from a discount courtesy of the merchants and your bank. Sometimes, just choosing to buy the same item but from a different store makes all the difference. Or maybe a 20% off deal will change your mind about what you wanted to gift someone? I know I’m a sucker for a deal, so when it comes to gifting, this is where I always start.

Amex Offers

Amex Offers


If you have a bit more patience, you sometimes can get smarter about it and do some stacking. This is definitely not for those last minute purchases in most cases, as it does require some waiting in between steps. In this case, you can for example, take advantage of a 10% offer at Staples and buy $200 worth of Macy’s gift cards for $180, and once you get home, you can buy the article you wanted from Macy’s by going to a Shopping Portal to take advantage of the 4x earning on Alaska Airlines.

This is my favorite kind of triple dipping. You’re getting your regular miles/points through your credit card spend. You’re getting your bonus miles/points through the shopping portal. And you’re also saving a percentage of your overall price as you’re not paying the full price on the item. 

Additionally, if you’re going for the Cash Back options, an easy way to stack is to use one of your cash back earning cards while going through TopCashBack and double dip on that cash back.


Yes, I know. You’re probably in tears after you did the math of all the miles you flushed down the toilet this Holiday season. But guess what? Christmas is only a year away, and now that you’ve learned how to squeeze the most juice out of these oranges, you should implement it next year.

Heck, you should implement it on the daily, not just for Christmas. This is one of the strategies that allow us to rack up literally over a million miles a year when combined with other avenues.

Do you have any other suggestions to maximize mileage or cash back earning? Let us know!

Author: Ben Nickel-D'Andrea

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