8 Tips to Hack Your Way to Travel More and Better

Travel hacking: are you new to this idea or perhaps only have dipped your toes a bit into what is affectionately known as the game? Travel hacking can be thought of as maximizing how you travel – and can be as simple or complex as you want it to be. Here are some important ways to shift your thinking and concepts to have in mind to help you get started and tips to build a foundation to help set you up for success! I am focusing this list to define travel hacking as maximizing credit cards, bonuses to get more points and miles to minimize your travel costs. So if you wanted to travel better (but cheaper) and are not in a position to get a credit card now, this list will be more beneficial.

1. Figure out your “WHAT(s)/WHY(s)”

The starting point should begin with: WHAT do I want to accomplish? This is a highly personal question because only YOU can answer this. Remember that there is no wrong answer here because what you want doesn’t have to be what another person or even I want from travel hacking. And be prepared that this is like life, in that your wants will be constantly evolving – maybe even from trip to trip. Some ways to think about this are ~ do you want to be able to: save as much money as possible? Stay somewhere on your bucket list? Take an aspirational business or even a first class ticket? Travel more? Save money on hotels/airfare so you can spend more on experiences? WHY is secondary and may simply be to be able to travel more or be a bigger goal with being able to have your kids see and experience more of the world to something as profound as finding/defining yourself again through travel.

Why start here: there are so many people that are now travel hacking and in combination with social media, comparison is the thief of joy. It’s hard to know what is true/how much is true with social media right? So just remember that if you’re traveling and were able to do what you set out to do then you’re doing great! I have seen so many people ask on forums how they did on their first redemption and you can feel their excitement slowly like a balloon with a small hole or worst, burst like a bubble with the comments. We’re all at different points in our journeys and it’s easier to feel the joy this should inspire by being able to travel by referring back to your WHAT/WHY.

The credit cards that I have that have annual fees!

2. Embrace that credit cards especially with large sign up bonuses (SUB) will be your best way to quickly build up points balances. This is travel hacking at its finest since it’s doing something in a novel and clever way and earning miles/points without flying and staying in hotels is pretty innovative. Caveat: please only consider if you pay off the credit card IN FULL every month because no reward amount can justify interest charges as the amount you pay will always exceed any rewards you earn! If you are new to credit, here’s a little primer.

Besides traveling for work, there is no other way to gain as many points/miles quickly than getting a rewards credit card. And if you are traveling for work, I would see if your company would be willing to reimburse you if you put the travel on your credit card – this will build up your points even faster especially with SUBs! The way to be successful with this particular hack is to NEVER spend more than you would have to get the SUB so it might be necessary to time your sign ups with big purchases or it may be worth it to prepay utilities if needed. And since many of you are local to me: did you know that Denver allows you to pay your property taxes online with a credit card with NO fees? I don’t escrow for my mortgage so every year I pay my insurance (home and auto – again with no fees and actually get a discount since I pay for the full year) and this is how I get a new credit card or two and meet the SUB(S) every year. Outside of this spring time frame, I typically wouldn’t spend enough to meet the SUBs….and that was true before 2020 when I was traveling so much as most of my flights and/or hotels were free with travel hacking!

3. Understanding the concept: CBA (cost benefit analysis) So many of you will balk at this and it might be helpful to know that many years ago I was also you: “but there’s an annual fee (AF) – why would I do that when I have XX credit card that is FREE?” So here is where you may need to change your thinking and also employ applying a very pared down version of this concept.

First, let’s delve into the idea of AF – I started to think and explain them differently in that these should not be lumped into the category of a late fee or worse ticketing fees for concert tickets since we all HATE those (ugh Ticketmaster and AXS)! But think about AF more along the lines of a subscription service: you are paying for access to be able to collect points faster than without this service. And when you frame it within CBA: it is more apparent that the AF will more than pay for itself as not only will you be earning points that far exceeds what you would get with having put this on a no AF cash back card.

Let’s do a quick dive with the card that I typically steer people towards if they have good/excellent credit and what I consider to be a great card for nearly everyone: Chase Sapphire Preferred. This card has a $95 annual fee and currently has an ELEVATED SUB of 80k! Let’s say that you spend $5k to meet the sub with $1K in 3x category of dining/steaming services/online groceries, and the remaining $4K at an earn rate of 1x. You have now earned 87K total: (SUB 80k + 3K + 4K). Chase values each point as $1/100 so that valuation would be $870. But most (including myself) would consider these points to be worth twice that and the value is $1740. While technically points aren’t worth anything until redeemed, we’re needing a $ amount to do CBA. Benefits $1740 – costs $95 = $1655 compared to a no AF cash back card that gives you 1.5x or 2x cash back amounts of $75 and $100 respectively!

There’s so much more to that card that is covered here that makes the CBA even more mindblowing. If you do decide to get the card, please consider using my referral link. Full disclosure, I do receive a referral bonus ~ so it’s mutually beneficial! Plus I’ll sweeten the deal: if you’re approved for the card and used my link, I’ll give you $50 credit towards baked goods. This can be for the Sapphire or lol any of the other cards I can refer you to!

4. Understanding that not all points and miles are created equally:

This concept is one that trips quite a few people up because it doesn’t quite make sense at first why the Sapphire Preferred card is typically recommended to start as the first credit card (besides the exceptional value vs $95 AF) is that you earn a flexible currency – Chase Ultimate Rewards (UR) vs earning miles or points. The reason why this is helpful is that you are not limited to just one hotel or airline when you go to redeem your UR – Chase has many transfer partners and will run periodic transfer bonuses for these partners allowing you to get even more bang for your buck.

That’s not to say that co-branded cards don’t have a place as you advance with in your travel hacking journeys. If you currently have one or two, it still might make sense to keep the cards especially for hotels as those cards can come with a free night greatly outweighing their AF. But knowing that not all points are created equal is very important when you are looking at SUB since you might be inclined to say that there’s a Hilton with a SUB of 130K points which is 50K more than the Chase Sapphire! Hilton hotel rooms tend to be 70K-90K/night for popular destinations such as NYC for a weekend night and can go up to 150K for a standard room for certain destinations (assuming you can find availability!). It’s just easier to have something that isn’t tied up to one entity – think about it as if you were able to earn dollars that you can spend anywhere versus points that you could only spend at Walmart or Whole Foods.

I was able to visit places like the Galapagos by saving money on flights during my months long travels through South America.

5. Applying the formula CPP (cost per point) and the concept: ROI (return on investment)

Let’s take a look first at CPP which is simply how much you would pay in cash for travel minus any taxes/fees that you would pay if using points (in cents) and divide by the number of points needed for the award. If you’re looking at booking a hotel room that costs $150 or 10,000 points, you’d be getting a value of 1.5 CPP. $100 x 100 cents/dollar /10,000 points. I have a love/hate relationship with this formula and especially it’s prominence when discussing redemptions. I think of this more as a guide to have more than a specific number that you must always hit especially considering that the $ portion is often inflated. Most people would not have paid the cash fare for business class seat so it’s not really fair to compare that redemption to a family that would have paid $ for a hotel room but instead used points – the former has an artificially high CPP compared to the latter. Remember your WHAT/WHY – you will find that sometimes it make more sense to pay cash and save your points but there are just as many valid reasons why it may make sense to use the 10K points in the example above if it allows you to be able to meet YOUR reasons even if others are saying that it’s a poor redemption since they always aim for at least 2 CPP. If you want to have a baseline number: as long as your redemption is above 1.25CPP ~ consider it a great use of your points (this is what you would get if you used the Chase Portal BUT see my advice re that route below!)

Also why I think that ROI is important to think of as it doesn’t just apply to finance or business but also to “the game”. Before I dive into what ROI is, always a good reminder that there are multiple ways to approach travel hacking and for some people, this is similar to sport with lots of training and dedication to get the absolute highest (and inflated) CPP and for others, this will be more relaxed and they are fine with good enough for them redemptions as each person has their own personal WHAT/WHY. And now back to ROI, it’s a calculation of the monetary value of what was gained versus the costs associated. This is different in terms of the CBA that was discussed earlier as the costs here are not what AF are on the card but costs would be considered the time spent figuring out how to use your points and what is gained should be thought of as the difference between what happens with low vs med vs high effort. And this can be frustrating at first but as with all things, practice makes perfect. What it boils down to is that the more effort that you put into this, the more that you will get from it and yield a higher ROI. If aspirational travel isn’t your jam or you can’t put in the time, you still need to be able to perform award searches minimally. To be able to book business or first class tickets at saver rates or on dream/aspiration airlines does take a lot of work and a bit of luck. What is luck anyways but opportunity meeting preparation for award searches so put yourself in a position to succeed which segues nicely into the next tip:

7. Flexibility is key and be prepared to quickly act!  

When you are booking flights and hotels for popular destinations during peak season, you will be able to leverage your points better if you are flexible. My buddy was able to get a killer deal to Paris (here’s how we did it) by leaving a day earlier. If you are looking to book award flights – you normally have to start looking the moment it is released if you are searching for the more elusive and scarce business or first class awards OR if you have flexibility (or if you are comfortable with booking refundable fares in hope of something popping up), I can attest that waiting to look three months out has been successful but often times, the absolute best availability for those seats become available a week to a month out. I was able to snag an EVA business class seat literally TWO days before I left to Thailand (with the most EPIC redemption I had ever pulled off!). When booking award flights, the key is to act quickly because those highly coveted seats may not last – often, it might be beneficial to put the reservation on hold. This will allow you to make sure you can take the time off and see other arrangements will pan out and better to lose a small fee if things don’t work out then missing out a great redemption that was quickly snatched up by someone else if things can line up!

FYI – it is easier to start award booking with hotels because it is less complicated with not needing to know airline alliances/code share partners and/or getting positioning flights, etc. I am partial to Hyatt (partially due to nostalgia from all my time with them and also they really remind me of SPG – RIP my fave loyalty program but I digress as usual). Hyatt with its WOH loyalty program has some of the best values for redemptions due to an award chart still being used combined with reasonable award rates. Unfortunately, they do have a limited footprint worldwide compared to Hilton, Marriott, IHG but that is rapidly changing with all of their acquisitions the past few years.

8. Resources/Help 

Some of my fave websites/apps and links to them because you don’t have to know it all, you just have to know where to look:

I first wrote this in 2016 and it’s been incredible how widespread travel and credit card hacking have gone seen then – I find myself often in Facebook groups (10x Travel, MilesTalk) to crowd source information and also to get some inspiration (there are some EPIC things coming down the pipeline that I will share as I figure out how logistics). But I balance that out with searches on my own and really have been loving Upgraded Points lately – but seems like that I end up reading articles from the Points Guy often. I am not linking a specific site here because this really has become so mainstream that simple google searches are now pretty effective and how I typically start when I am thinking about a trip or want to know which airlines have “sweet spots” for redemptions.

Flyertalk: There are so many people who are even more obsessed and crazy about the above two things than I am and I have learned so much in their forums. This is the OG in the world of travel hacking and full of great information and knowledgeable people BUT it is so hard to search if you don’t know where to look, can be overwhelming, and could use some updating to be more userfriendly..just a warning. But if you start to really get into this or you want some great intel, it cannot be beat.

Google Flights: A useful, fun, addictive way to search and save on flights

Rome2rio: Such a cool website/app to “Discover how to get anywhere by plane, train, bus, ferry and automobile” – as it has gotten more popular, I have found that some information can be outdated but still has proven itself to be handy for me.

*I personally stay from OTA (online travel agencies like Expedia or booking.com) and using the Chase portal for any of my trips. I know many have and will say that they have never issues with third party bookings and I am sure that is true but when there is a problem, I want to be able to have the airline or the hotel assist me. When you use an OTA, your purchase is with them directly and that curtails what help a hotel or airline can provide and I have seen way too often how that comes back to nip people in the bud. I just put this out there because if you do decide to go that route, you should know that when you are told to call Expedia or booking.com, stop yelling at the front desk agent or the gate agent at the airport and call the OTA because it was your decision. Plus – for hotels, you do not earn elite night status nor are entitle to your elite perks.

Bonus tip: Make an impact with your money (and why it’s not 9 ways because eight is my FAVORITE number lol)

It’s a privilege to travel. Saying this doesn’t undermine the sacrifice or hard work that one may make to go someplace but it does acknowledge that not everyone has this luxury/right. Money is important and can help make a big difference based on how it’s spent. I love supporting local businesses and also seek out places that have a greater social mission. And also choose to support places that are ethical/humane ~ so no elephant riding or tiger palaces and so forth for me.

Placemat from Haven in Siem Reap

My WHY: is that I want to live life to fullest and for me, travel is a huge part of who I am. My WHAT is simply to travel more and the adage about the best money is spent on experiences holds especially true for me. Yes my hot air balloon rides were expensive but I will always remember those magical sunrises over Bagan, Burma or Cappadocia, Turkey as seen below. Travel hacking had allowed me to use points/miles for flights so that I could spend my cash on experiences like this!

Hopefully there was something or a number of things that will help you with maximizing your money for travel! Did I miss anything here that you think is a great money & travel tip? Or is there a subject that you wish I had gone more in depth about? Please let me know and I’ll see if I can work it into an upcoming post! 


2 Comments Add yours

Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s