5 Simple Steps to Start Travel Hacking

Miami to Grand Cayman American Airlines pilot Timmy
Flying to Grand Cayman
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For those of us who love to travel, but have limited funds, you can’t help but be envious of all the vacation pictures we see on social media.  But what if there was a way to travel more often while using less money?  I’m here to show you how to start travel hacking using airline miles and hotel points so you can vacation like a rock star while spending money like Mr. Scrooge using some very simple steps.

5 Simple Steps to Start Travel Hacking

There are plenty more advanced steps to maximize your miles and points, but, for now, let’s focus on these 5 simple steps to start travel hacking.

Step 1 – Know where you want to travel

As Stephen Covey says in “The 7 Habits of Highly Effective People“, you have to begin with the end in mind.  If your heart is set on traveling to Europe or Asia, earning 1,000,000 points with Southwest Airlines isn’t going to make it happen for you.

start travel hacking. Jekyll Island Scarlett beach
As you can tell, Scarlett enjoyed the beach very much!

Similarly, if your favorite hotel chain is Kimpton, like mine is, understand that they don’t have any locations in Mexico.  And remember that many hotel chains have multiple brands… for instance, Starwood Preferred Group (aka SPG) has multiple brands, such as Westin, W, Sheraton, and Aloft to choose from.

When you start travel hacking, you want to pick an airline and hotel brand that will get you to the locations you want to travel to most.

Step 2 – Know how you want to travel

Some people want to travel as often and as much as possible, so they’re ok with flying Economy; while others value aspirational travel, which is luxury travel that they otherwise could not or would not pay for.  I am fine with traveling in Economy (Southwest is my favorite airline, after all) when flying across the US or to Mexico.  However, when flying to Europe, Asia, or Australia, I prefer to fly Business or First Class.

start travel hacking. Timmy in lay flat business class seat
Timmy (26 mos) in Business Class flying back from Paris & Spain

If your goal is to get pampered while you fly and enjoy the perks of Business or First Class, discount airlines like Spirit, Frontier, and Southwest are not the programs for you.  They do not offer premium cabin space, so you will be disappointed if you’re trying for Business or First Class.

For hotels, most chains offer a range of properties, from discount to high-end.  However, some do not (or their “high-end” compares more to mid-range properties from other chains)… so pick wisely.  In the case of hotels, you want to understand how quickly you can have access to the high-end properties based on your point-earning abilities.  For instance, Hyatt and SPG are many people’s favorite hotel chains.  My favorite is Kimpton based on how special they treat me when I stay and my ability to earn free nights that are good at any of their portfolio properties.

Remember, you are better off concentrating your flights, stays, and spend among a couple of brands, rather than having “orphan” points spread out among a handful of brands.  Orphan points are those that are not enough to redeem for a flight or a stay and will eventually be wasted due to expiration policies.

Step 3 – Pick your brands & focus your spend with them

After you’ve selected the airline and hotel brands that suit the Where and How you like to travel, the key when you start travel hacking is to focus all of your travel spend with those brands.  When you’re searching for airfare or a hotel stay, it makes sense to pay a little extra to stay at your favorite brand vs. one that isn’t your favorite… even when the flight or hotel properties are very similar.  The reason is Loyalty!

By being more loyal to your favorite brands, you will earn more benefits and get closer to reaching higher status levels.  As you reach higher status levels, you will receive priority boarding and service with the airlines and better rooms and perks at hotels.  For instance, you can check into your room earlier and check out later and receive free upgrades to nicer rooms when available.  I’m an Inner Circle Member (the highest level) with Kimpton, so even though I only pay for basic rooms, I often get upgraded to one of their nicest rooms available.  Here’s a picture of my upgraded Santa Monica room at the Kimpton Hotel Wilshire in Los Angeles.

start travel hacking. Kimpton Hotel Wilshire Santa Monica suite dining area
Kimpton Hotel Wilshire Santa Monica suite dining area

Step 4 – Get the card that earns the most — bonuses, benefits, and transfers

Credit cards are an excellent method of earning points, benefits, and loyalty with airline and hotel brands when you start travel hacking.  Most major airlines and hotel chains offer a branded card from one of the major banks, like American Express, Citibank, Chase, Barclay, Bank of America, and US Bank.  These cards often come with instant upgraded status, just for having the card… even if you’ve never stayed with that hotel!  For instance, the Chase IHG Visa provides instant Platinum status with IHG (Holiday Inn, Interncontinental, Crown Plaza) and the both the Citibank and American Express versions of the Hilton card provide Gold member level status as long as you own the card.

These cards usually provide opportunities to boost your point-earning potential.  If you pay for your flight or stay, you’ll often receive bonus points for that spend.  And there are often bonus categories for spending at other merchant or merchant categories.  For instance, the American Express Hilton Reserve earns 6x points at grocery stores, gas stations, and restaurants.

start travel hacking. money-256319_640

When you sign up for credit cards, there is also an opportunity to earn sign-up bonuses that provide meaningful amounts of points in a short period of time!  I earn at least 500,000 airline miles and hotel points a year just from credit card sign-up bonuses from what people call “App Parties“.

Unfortunately, my favorite hotel chain, Kimpton, doesn’t have a credit card relationship, so I use other cards to pay for stays with Kimpton.  Which brings up another valuable point… just because an airline or a hotel has a relationship with a bank, doesn’t mean that their card provides you the most value!  For example, most people would assume that you should pay for a flight on American Airlines by using the Citibank American Airlines credit card, which provides 2x points for all spend with American.  You might be better off paying for that airfare with the American Express Gold card, which provides 3x points when buying directly from the airline (instead of sites like Hotwire and Expedia).

As an added bonus, American Express Membership Rewards points can transfer to many airline and hotel brands, you can redeem them for cash or gift cards, or use them to purchase airfare through an Amex concierge… this flexibility provides you with so many options.  Whereas, when your points post with American using the American credit card, you are stuck using them with American Airlines and their partner airlines only.

start travel hacking. American Express Membership Rewards points options

Amex Membership Rewards points transfer to airlines such as Delta, Hawaiian, British Airways, and JetBlue and hotels like Hilton.  Chase Ultimate Rewards transfer to places like United, Southwest, Marriott, and Hyatt.  Citibank ThankYou Points transfer to many places, such as Hilton, Ethiad, Qantas, and Singapore Airlines.

Step 5 – Earn points in alternative ways

Most people earn airline miles and hotel points through the one of two ways described above — paying for tickets & rooms or using the co-branded credit card.  But, when you start travel hacking, there are many other ways to earn miles, points, and cash back that you may not know about.

First off, I recommend following the 11 immediate steps when getting a new credit card.  These steps are good for your existing credit cards as well, so open your wallet, grab your cards, and ensure you’re not missing out on valuable benefits.  For example, you can earn additional miles and points when dining out through the Dining Rewards program mentioned in that blog post.

Two other important opportunities to earn miles and points are with shopping portals and rewards program partners.

By clicking first through a shopping portal before going to your favorite website to shop, you can earn many multiples of points on your order!  I usually go through EVreward.com first to see which programs are offering the highest bonus, then click through to that portal.

For example, I bought my Mom some flowers for her anniversary with my now-deceased Dad recently and earned a bunch of miles.  Here’s a sample of what is available through FTD.com when I researched on EVreward.com.

start travel hacking. EVreward FTD bonuses

Reward program partners vary by hotel and airline, however, they usually all have a partnership with rental car agencies.  So, you can often find promo codes on your preferred program’s website to save on your car rental, while still receiving the added benefit of bonus miles!  There are also cross-promotions among airlines and hotels, where you can receive hotel points AND airline miles when staying at select hotels.

Other promotions pop up from time to time as well.  Citibank offers American Airlines miles or ThankYou points for opening a checking account.  If you sign up for DirecTV, they’ll give you 25,000 American Airlines miles.  Southwest Airlines offers bonus points when booking rides on SuperShuttle.  And almost every airline offers points when signing up for email surveys through eMiles, eRewards, and ValuedOpinions.

There are honestly too many opportunities to list here.  The most important takeaway is to evaluate how you are spending your money… and with whom… to ensure that you are getting the biggest bang for your buck.  You work hard for your money, so take a few simple steps to have your money work hard for you and help you earn more, bigger, and better vacations!

Free Printable to download

Click this link or on the picture below if you’d like to download this printable as a PDF.

5 Steps to start Travel Hacking
Click here to download the printable!

The Bald Thoughts

There was a lot of material covered in this post about how to start travel hacking.  If you need help getting started or figuring out your next move, don’t hesitate to drop me an email.  I’ll be glad to help… all I ask in return is to sign up for our newsletter, use our links, and share our site with your friends.

Click here or on the picture below to be taken our free travel advice page.

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  1. While there are many helpful tips in this post, what resonated to me most is the “orphan points” warning. We have learned our lessons and stick with a few key programs. Now that Kimpton is with IHG, hoping you’re able to earn points for stays with the CC!


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