Points, Miles & Life

Travel adventures on this earthly pilgrimage

Category: Guides

West Coast Magic with Alaska Miles: A Primer

One of my favorite things in this hobby is figuring out how to maximize my miles. Earning miles via credit cards is easy enough, but they are only as valuable as you make them.

Alaska MileagePlan is one of my favorite award programs. Back in late 2016, they rolled out new distance-based awards, both reducing the price on many awards and raising the “cap” on others in high demand. The new awards are called a hop, skip, jump, and leap, based on the distance traveled. Here’s the chart:

Overall, I think consumers came out slightly ahead. Especially if they know how to maximize Alaska’s award routing rules. Here are some great options to explore with your Alaska miles:

Scenario 1: The one-way “round-trip”

One of the most unique things about Alaska Airlines award tickets is that they offer a stopover on a one-way award. Granted, the stopover has to be in one of their hubs, or a hub of a partner. I’ve found a few awards that break this rule, but it generally holds true.

However, if you’re interested in traveling to one of their hubs (think Seattle, Portland, Los Angeles, and Anchorage), you can often use this to your advantage.

Consider for a second that you want to visit Seattle from the Silicon Valley. At a distance of 696 miles from San Jose, a one-way flight *barely* qualifies for the lowest level Alaska award of 5,000 miles. But you can actually book a “round-trip” on a one-way ticket, if you’re willing to get creative.

Instead of booking a round-trip award to and from San Jose for a total of 10,000 miles, use the multi-search tool to add a different, but (sorta) close return airport, say Reno, Nevada. Looks like you even get to fly through Boise, for a total flight distance of 1,696 flown miles.

You’d expect this ticket to price out at 10,000 miles, given the flight distance. But it turns out Alaska prices award tickets on their own metal simply by distance between origin and destination! Because Reno and SJC are much less than 700 miles apart, this award will price out a 5,000 miles at the lowest level!

Now you just have to get yourself home to San Jose from Reno.  You could easily catch a cheap flight back, or maybe take Amtrak.

Sure, this may not be a desirable trip for many people, but what if you wanted to see Tahoe for a bit before heading back to the Bay? It could be just the ticket for you. You’re only looking at 5,000 miles and $70 for a two-stop vacation!

I’m mainly using this example as an illustration, although my wife and I did fly a “one-way” award from Arcata to the Bay Area, with a convenient stop in Portland to meet up with our in-laws (SEE: The Pacific Northwest Stopover Trick).

Scenario 2: The two-stop hop (aka the “in-laws”)

I’ve definitely had my in-laws in mind when considering some of the potential in the Alaska program. My mother-in-law often visits family in San Diego, typically flying out of the tiny Sonoma County (STS) airport. Since the route is under 700 miles, it prices out at 5,000 Alaska MileagePlan miles one-way.

But what if she and my father-in-law want to visit, say, Seattle for a few days, before heading to sunny southern California?

Utilizing Alaska’s amazing stopover on one-way tickets, you can actually book STS-SEA-SAN as a one-way ticket for the same 5,000 miles!

This is especially crazy given that the SEA-SAN flight distance is 1,050 miles and rings in at 7,500 award miles when booked by itself. Again, Alaska actually prices it based on the STS-SAN distance.

Tack on a cheap one-way, or another 5,000 mile award flight back to STS from San Diego, and you have a two destination vacation for a mere 10,000 miles. Not sure you can beat that.

Like the San Jose to Reno example, all you need to find is a cheap ticket back to Santa Rosa. Or you can burn another 5,000 miles, which will probably be worth it in this case. It’s still 10,000 miles for a two-destination vacation!

Scenario 3: The home “stopover”

Things get even more creative if you live in one of Alaska Airlines’ main hubs. Especially Seattle or Portland. The award routing rules are extremely advantageous.

Consider the scenario where you are taking two vacations in the western U.S. in the next several months. Say, one to San Francisco and the other to Las Vegas.

Instead of booking two round-trip awards, book a one-way for your first leg. Cash tickets for this route are competitive, so they may be the way to go instead.

Next, book your return, but combine it with your outbound to Las Vegas on the same one-way award (use the multi-city search tool). Bingo. Your “stopover” is now your several weeks at home between trips. And it is a crazy cheap 5,000 miles!

Now all you have to do is book your final leg and you’ve saved yourself up to 7,500 Alaska miles, the normal price of a SEA-LAS flight! Maybe later in the year you have a trip to Denver and another to Salt Lake City. You can pull this stunt again!

Scenario 4: Hawaii and a transcon on the same one-way

Let’s take the home stopover one step further. While useful before, this trick becomes even more lucrative if you combine a Hawaii trip with a transcontinental flight. For this example I still have to assume you live in an Alaska hub.

Imagine for a moment that you’re booking an award to Hawaii. If you’re located on the West Coast (I’m assuming you live in Seattle), hopefully you’re considering using British Airways Avios. They are generally the best currency for flying West Coast to Hawaii.

But what if you have a trip planned to the Big Apple a month after your Hawaii trip? Hold those Avios for a moment. Alaska miles will get you further, again with their amazing stopover.

If you plan this right, you can essentially get *both* one-way tickets on the same award, spanning two different trips.

Plan your outbound as a one-way with Avios (12,500 per ticket), and then plan your inbound as a one-way Alaska award for 17,500 MileagePlan miles. Add in a stopover in Seattle that spans your time at home.

Voila. You now have a one-way ticket back home from Hawaii, and then a one-way ticket to NYC, all for the less than a single flight to Hawaii would cost with many other mileage currencies.

Is it an awful red-eye? Yes. But for 17,500 miles, you can’t really complain (I’m sure you can find better flights if you book far in advance). Here’s another:

Honolulu back home to San Jose, before taking off for Alaska on another adventure.

Scenario 5: Rural Alaska

Flying to rural Alaska doesn’t really require any interesting “hacks” per se, but I find it is a fantastic use of Alaska miles. You can head to Barrow to experience 24-hour daylight, or maybe go hiking in Nome.

I mention rural Alaska since cash tickets are often super expensive. Consider this round trip between the Bay Area and Dutch Harbor. You’ll almost certainly spend over $1,000 on a cash ticket, if not closer to $1,500. You can fly the same trip for a mere 25,000 MileagePlan miles round-trip. Consider hanging out in Anchorage for a few days as well with your free stopover.

Frustratingly, there is far less award space available at the lowest level than there was last year. Because Alaska offers variable award pricing, you’ll probably end up paying more like 20,000 miles for the ticket. Still, this can make sense for destinations in rural Alaska that cost a ridiculous amount in cash.

A few issues

Annoyingly, Alaska Airlines still doesn’t recognize Bay Area airports as a “hub” for award routing stopover purposes under most circumstances. Given that the airline has bought Virgin America, I wish they would change this.

The system also knows some airports are co-located. You can’t book a “one-way” ticket from SFO to Oakland with a stop in Portland. Nor can you even return to Sacramento or Santa Rosa from the Bay. MileagePlan would be a gold mine if their system allowed these tickets.


I hope this has been useful in showing you how to unlock the potential of Alaska miles. Overall, the award price changes to the Alaska program have been good, but there are some quirks. Personally, I wish they would price awards on PenAir out of Arcata airport better.

If you’re not interested in domestic travel, there are a number of possibilities for using Alaska miles for some great premium products, like JAL and Cathay Pacific to Asia, and AirFrance and KLM to Europe. Business class awards to India on Emirates are also a decent deal.

Header image courtesy of Frank Kovalcheck under CC 2.0 license

A Simple “Travel Hacking Starter Plan”

Recently, I’ve laid out several beginner posts now about getting started in the travel hacking game. I’ve recommended a few cards and laid out some ground rules for managing your travel credit cards.  There are even 2 great airline cards I recommend for Humboldt locals. Check out these posts, if you haven’t already:

These posts provide a lot of help to get going. But now I’d like to offer a basic (but full) ” travel hacking starter plan” that should be suitable for most people interested in getting into this game.

Step 0: Check your credit

This is one thing I haven’t mentioned before, but it is essential. You should check your credit. Actually, you should probably monitor your credit routinely. Many people don’t. I typically check my credit and my wife’s credit twice per year. You are guaranteed a free credit report each year by law. The best site to pull your credit report (the free one per year) is annualcreditreport.com.

You can typically also get your credit report from any of the big three agencies for free or for $1 if you sign up for a free trial. I sign up, print off my report, and then call to cancel right away. If you don’t cancel you’ll be charged the monthly service fee.

Your credit report may or may not give you your credit score. I know the free annual one does not, at least last time I used it. Knowing your score is critical as well, since it is typically what determines whether a financial institution will approve you for an account or not.

At the end of the day, you need to have a good to excellent credit score for travel credit cards, typically above 700. My credit has been at or above 750 for most of my adult life, and I have had little trouble being approved for the vast majority of cards.

Step 1: Make a plan

This one hearkens back to my previous post on beginner travel hacking tips. I highly suggest that you come up with a plan, and do some research to figure out which programs and points/miles you should collect to get you to your goal quickest.

Travel Hacking Starter Plan

If you don’t have a set plan and are still interested in jumping in, then you really can’t go wrong with the next step…

Step 2: Apply for the Chase Sapphire Preferred

For most people, plan or no plan, the Chase Sapphire Preferred is the best card to start with. You typically need excellent credit to be approved. The average score needed from one poll is 736.

Starting with the Chase Sapphire Preferred is good for two reasons. First, it has a good sign up bonus that offers flexible points, keeping your redemption options open. Second, you won’t be subject to the “5/24 rule” if you are new to the game. The “5/24 rule” is essentially an informal policy Chase has put in place where they will not approve you for certain types of cards if you have more than a certain number of new accounts (typically 5) opened in the past 24 months. Going with this card early means you won’t be aced out of it later due to “5/24”.

The Chase Sapphire typically offers a bonus of 50,000 points after spending $4,000 in the first 3 months of card membership. The annual fee is $95, but it is almost always waived the first year, per the terms of the offer. As I mentioned, the points are flexible and can be transferred to a number of loyalty programs. If you are interested, I would appreciate it if you would leave a comment or send me a note via the contact page so I can send you a referral link.

If you want to go big and understand the cost/benefit, consider the Chase Sapphire Reserve. It is a step up from the Chase Sapphire Preferred, but it carries a $450 annual fee, additional perks, and higher earning rates.

Step 3: Apply for a Chase Freedom

This card goes fantastically with the Chase Sapphire Preferred. The Freedom offers rotating categories of 5% UR points, and if you can transfer these to any other UR earning card. This means that if you have the Chase Sapphire Preferred (or Ink or Reserve), you can use the Freedom-earned UR points in the same way you use points earned from those cards. You simply need to transfer them to your other account. This can significantly increase the value of your UR points. Without pairing a Freedom with a “full” UR card, you’re points are only redeemable for cash back.

Personally, I only have the standard Chase Freedom. There is also the Freedom Unlimited, which does not have rotating categories, but it does earn 1.5% back (1.5 UR points) on all purchases. Many people prefer the Freedom Unlimited. I find that my Chase Freedom spending is….limited, so I tend to just try to maximize the rotating categories as I can.

You might consider pairing an application for this card on the same day as the one for your Chase Sapphire Preferred, if your credit score is goo and you’re feeling gutsy. Chase has been known to approve you for more than one card per day, and you will reduce the number of “hard hits” on your credit report. Each application normally does a “credit pull”, but the two pulls will be combined if you submit two applications in one day. Do note that you will probably have to talk a phone rep into approving you for the second card. Absolutely apply for the Chase Sapphire Preferred first, though. 

The other benefit of a Chase Freedom card (or Freedom Unlimited)? No annual fee!

Again, like the Chase Sapphire Preferred, if you’re interested in the Chase Freedom card, please leave a comment or send me a note via the contact me page so I can send you a referral link. You’ll earn me a few points. 🙂

Step 4: Learn how to use your points

Getting your cards in hard and using them to accrue points is only half the equation. The other half is learning how to put them to good use.

By focusing on the cards in the Chase Ultimate Rewards (UR) program, you’ll be set up with points that can be transferred to some of the most lucrative loyalty programs, along with some of the easiest to use. I suggest signing up for all of them. You can then save your loyalty number to your UR account. My favorite loyalty programs affiliated with the Ultimate Rewards program are:

  • United
  • Southwest – Sometimes
  • Hyatt – The only really good hotel partner

On of our best award redemptions was at the Hyatt Regency in Nice, France

Other good ones:

  • Korean
  • Flying Blue
  • Singapore
  • British Airways – Specifically, west-coast U.S. to Hawaii

Explore some of these programs. Look up their award charts. Figure out their routing and award redemption rules. Find the sweet spots. It may seem overwhelming at first, but you’ll get better the more you learn.

You can also use Chase UR points for travel through the Chase portal at 1.25 cent per point (1.5 cents if you have the Chase Sapphire Reserve). This can be a great way to book flights outside (or within, even) the UR transfer partners.

The Chase points are also worth $0.01 each, so having to cash them out is also a reasonable option. Life happens, and sometimes cash in hand is better than travel later. I get that.

Step 5: Plan a trip with your points, even if it is small

Put what you have learned to good use. I suggest a domestic trip, or a trip to Hawaii. A quick example:

  • Two domestic tickets in United saver economy: 12,500 per leg * 2 legs * 2 people == 50,000 United miles == 50,000 UR points (transferred to United)
  • Category 2 Hyatt hotel for 4 nights = 8,000 points per night * 4 nights == 32,000 Hyatt points == 32,000 UR points (transferred to Hyatt)

There. You have a long weekend getaway anywhere in the U.S. with United award availability for 82,000 Ultimate Rewards points. If you include the bonus on the Chase Sapphire Preferred, plus the authorized user bonus, plus the Freedom bonus, plus the points from spending required to get both bonuses, you’ll already have 69,500 points. You’re most of the way there.

Travel Hacking Starter Plan

United is an easy domestic award option – Photo: Boulder, CO & Front Range

Domestic U.S. trips typically require far fewer points, so I suggest you start there. But if you want to plan a multi-stop trip to Southeast Asia on a double open jaw ticket with a free Excursionist Perk extra leg with your United miles, be my guest. There, I probably scared you off…

Step 6: Branch out

Once you have completed your first free or mostly free trip, branch out to other cards. You’re obviously more than welcome to branch out before that if you have a good handle on things. Some other card suggestions:

  • Starwood Preferred Guest American Express card (before it goes away)
  • IHG MasterCard (great hotel card)
  • United MileagePlus Explorer Card (let me send you a link)
  • Hyatt Visa Card (2 free hotel nights…play in 2P mode and have your spouse get one, too)
  • American Express EveryDay card (great for groceries, accrues transferable points)
  • Chase Ink Preferred (if you have a small business)

Final Thoughts

I will continually stress that you must be responsible with credit cards. No, credit cards are not bad, but you can turn them into something really bad when misused. Pay your balance off on time and in full each and every month.

Other than that, have fun! This is a great hobby to be in, and I hope this travel hacking starter plan is useful. I’ve just hit 5 years since getting my first couple travel credit cards and using them for a wonderful honeymoon. You can read all about that if you want.

5 Commandments of Travel Credit Cards

One of the hurdles some people face when considering the travel-hacking game is properly understanding credit cards. Many err on the “credit cards are evil” side of things, and prefer not to deal with them at all. Others rush in headlong and quickly find themselves in over their heads. Consider this story as an poignant example.

Know your limits

Please don’t get a credit card if you know it will cause you to get into debt. You’ll be far better off without it. Rewards are great, but they don’t matter if you’re spending more and/or going into debt to accrue them.

If you have difficulty managing your spending and/or tracking your purchases, consider wisely the choice to use a credit card. If you end up $2,000 in debt after accruing points for a “free” family trip to Hawaii, your trip is suddenly no longer free.

The commandment of properly using credit cards

If/when you do have a travel credit card (or any credit card), here are 5 commandments you should abide by:

  1. You shall not miss a payment – This one is the biggest. Missing a payment will result in a late fee, not to mention have potential implications for your credit score for missing a payment. If you miss a few payments, you can cause your credit score to plummet. You’ll also be paying the bank needlessly and negating any rewards you’ve gained. Use your card wisely, and don’t accrue more in charges than you can pay off by your payment due date.
  2. You shall not pay interest – Even if you make your payments on time, you will still get hit with interest unless you pay the statement balance in full each month. Do not let this happen! Each time you pay interest you are negating any potential benefit of using you card to earn points, and typically setting yourself even further back than the value of the rewards.
  3. You shall not fail to earn a sign-up bonus – When you sign up for a new card, be sure you understand the terms of the bonus. There will almost always be a spending threshold that you must achieve within a certain time-frame, typically $1,000-$4,000 within the first 90 days. My wife and I have only missed one sign-up bonus, and it was a really sad day when I realized our error. We failed to earn 50,000 Delta miles because I thought the spending threshold was only $1,000 when it was actually $2,000! Do note that fees (such as an annual fee) do NOT count toward the sign up bonus spending requirement! Only net purchases (purchases – refunds) count.
  4. You shall not cancel a card without good reason – You should always have a good reason to cancel a card. It may be as simple as “I don’t want to pay the annual fee.” Remember that the more credit you have can actually increase your credit score (SEE: The 5 Factors that Influence Your Credit Score), generally because it drops your utilization ratio. You can increase your score by keeping accounts open that do not have an annual fee.  As these accounts age, they will improve your score. Do not cancel a card simply because you do not use it much, especially if it doesn’t have an annual fee.
  5. You shall not forfeit rewards by canceling a card – Co-branded credit cards (those associated directly with a loyalty program) generally have rewards that are independent of card membership. That is, they aren’t forfeited when you cancel. For example, once my points have posted from my MileagePlus Explorer card to my United frequent flyer account, they are mine. I would not lose them if I canceled my card. Bank cards are different, however. When you cancel a card, you may lose all the points in your account. Make sure you understand the various program rules before you cancel a card! Sometimes it’s as simple as transferring the points to a partner program, or cashing them out.


I want to reiterate that credit cards are not for everyone. If you have difficulty managing your spending and/or tracking your purchases, then you may want to steer clear of them. If you end up $2,000 in debt after using points for a “free” family trip to Hawaii, your trip is suddenly no longer free.

4 Beginner Travel Hacking Tips

If you are new to the travel hacking game, especially on how to use credit cards to earn oodles of miles and points, you may struggle to digest the huge amount of information available. There is so much on the internet that it may seem overwhelming. But don’t let that hinder you from getting started.

You may have lots of questions: how can I obtain free flights to [insert place]? What credit card is the best one to start with? How do I redeem the points and miles I earn? Should I be worried if a card charges an annual fee?

There are answers to all those questions, but they may be different for each person. For some, paying an annual fee simply won’t do. For others, it may be totally justified if the rewards are worth it.

You will need specific answers, but make sure you have some guiding principles in place. Here are my four beginner travel hacking tips for those just starting the miles and points game:

  1. Have a plan – Don’t apply for credit cards until you have a plan. It doesn’t need to be a fully developed plan, but you should have a goal in mind. It could be something like “travel to Hawaii in 2018 with my family of 4”. Having a specific trip or goal in mind allows you to focus your efforts on attaining that goal. Admittedly, I have sometimes applied for a credit card without considering how I will be able to use the points, but this isn’t the ideal strategy, and I certainly didn’t operate that way when I started out. I had a very specific goal in mind. Identify a goal, find a couple credit cards that will help you achieve that goal, and pull the trigger. Then, once you have the cards, learn the ins-and-outs of those specific programs.4 Beginner Travel Hacking Tips
  2. Start slow – Don’t rush into the travel hacking game. If you told me you got 27 credit cards your first year, I would probably raise an eyebrow. Maybe two. It has taken me years to be comfortable applying for a large number of cards, to understand the ins-and-outs of various loyalty programs, and to be able to earn and redeem hundreds of thousands of miles and points each year. Don’t rush. Learn the ropes first with a couple cards (that you’ve identified in your plan) before continuing down the travel hacking path. You’ll get better over time, trust me.
  3. Understand your financial situation and abilities – The travel hacking game isn’t for everyone. There is a lot to learn and understand. If you need simplicity, you may want to use a single good cash back card for a while before venturing further. Also, cards with annual fees aren’t for everyone. Personally, I keep several cards that charge an annual fee, but that is because the value they provide my wife and I is much greater than what we pay for them. But not everyone will see things the same way. Also, if managing your finances is generally a struggle and you do not have a budgeting system in place, credit cards may simply not be the thing for you.
  4. Do your research – Don’t apply for a credit card just because some blogger on the internet says it is the best card of the year. Some are paid commission to offer certain cards, and they’ll often sing their praises on a weekly basis. The card may or may not be something that is actually provides you value. I will recommend certain cards at times, and even then, do your own research to see if it is something that is a fit for your plan. There is also a ton to learn when it comes to redeeming points and miles. Make sure you research various programs. Also, the award travel world tends to change, so research is still imperative even once you have a basic handle on things.


These four beginner travel hacking tips will help you stay on track as you get into this game. Lots of people do crazy stuff with their points, and it’s easy to think either (a) it’s too difficult for me or (b) it’s too good to be true. I’m here to tell you that with a little planning, research, and practice, you can be doing amazing things with your own points and miles.

As a recap: have a plan, start slow, understand your situation, and do your research. You won’t go wrong.

If you live locally and are interested in a starter course in “travel hacking”, I’ll likely be offering one on a Monday evening in March or April. Details should be released this week!