When it comes to lucrative side hustles, travel hacking tops my personal list.

My own journey dates back to 2010, when I purchased Chris Guillebeau’s Frequent Flyer Master…. (Now updated and called The Unconventional Guide to Luxury Travel on a Budget).

My first “hack” was booking a flight for two from Chicago to San Francisco with the Continental OnePass Plus MasterCard (this ages me a bit). A few months later, I booked two first-class tickets one-way from Chicago to Buenos Aires.

I’d estimate this side hustle has saved me upwards of $30K+ in travel expenses over the years. More so, I’ve had the chance to experience many things I wouldn’t have been able to

What I’ve Been Able To Accomplish

I consider myself a conservative travel hacker. There are people out there a lot more aggressive and better skilled at this game then myself.

Yet, looking over the past year, I was able to save a good amount of money.

  • $2,000 in statement credits through sign up bonuses (Value $2,000)
  • 4 Round trip flights from Chicago to Kauai (Value = $2,824)
  • 2 Round trip flights from Chicago to Phoenix (Value = $450)
  • 5-Night stay at the Phoenician in Scottsdale (Value = $1,345)
  • 4 One-way flights from Chicago to Fort Myers (Value = $480)
  • 1 Round-trip flight from Chicago to Dallas (Value = $220)
  • 20 Day standard car rental in Kauai (Value = $1,250)

Total Estimated Value: $8,559

There are no doubt I find for the 10-15 hours a year I invest in travel hacking well worth the effort.

If you really want to maximize your rewards, sign up for the free email course: The Beginner’s Guide to Free Travel Through Credit Card Rewards below:


Whatever your goal may be — whether it’s travel more or earning money on the side, here’s 8 tips to maximize your rewards.

*This is a more travel than usual. The reason being we had Baby # 2 around 30 months ago. So, there was very little travel the month’s prior to our addition and for about a year after. 

The Disclaimer

I’m a Certified Financial Planner™/personal finance nerd who has worked hard over the years to develop some good financial habits. What I do works for me because I know my cash flow, expenses, and control my spending.

If you’ve struggled in the past with credit cards — this is a game you’ll lose BIG at. No rewards you could earn are worth the price of credit card interest.

8 Travel Hacks That Save Money

# 1 – Choose The Right Card To Maximize YOUR Everyday Spending

When looking at different credit card offers, it’s important to choose a card that maximizes your spending. For example, if you don’t eat out a lot, it doesn’t make sense to have a card that earns 3X points on dining out.

More so, you don’t want to increase your spending just to earn points because that’s certainly not the goal.

One credit card that’s useful to maximize your spending is the Chase Freedom Card.

I first applied to the Chase Freedom Card 10+ years ago in college. Yet, I still find myself using this card often.

The Chase Freedom Card comes with:

  • A $150 bonus after you spend $500 on purchases in your first 3 months from account opening.
  • No annual fee
  • 0% intro APR for 15 months from account opening on purchases and balance transfers. The balance transfer fee is 3% of the amount transferred with a minimum of $5.

The best aspect though of the Chase Freedom card is you’re able to earn 5% cash back on up to $1,500 in combined purchases in bonus categories each quarter.

Compare this card with other top cash back cards

# 2 – Get At Least 1.5% Cash Back On Your Purchases

For non-bonus category spending, I put most of my spend on the Chase Freedom Unlimited.

The Chase Freedom Unlimited card earns 3% cash back on all purchases during the first year on up to $20,000 spent. After the first year, you’ll then earn 1.5% cash back on all purchases.

As I value Chase Ultimate Rewards Points for their flexibility, I choose to get 1.5% back.

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# 3 – Use Your Rewards!

Rewards don’t accrue interest and lose value over time through devaluations.

Cash invested, on the other hand, gains value over time.

This is why it’s important to accumulate points with a purpose. If not, I like to turn my points into cash.

Looking at what I used my points on over the past year, an experienced travel hacker could get more value. For example, exchanging Chase Ultimate Rewards for $2,000 in cash, would make most travel hackers cringe.

As a family, we plan out our travel 18 months ahead of time. We then look at what we need to do to achieve our travel goals within the next 18 months.

If we’ve accumulated points that are not going to use within 18 months — we try to turn those points into cash or immediate savings (such as booking a car rental, which isn’t a great value either).

# 4 – Know Your Credit Score

My # 1 reason for not playing this game sooner was now knowing how it would impact my credit score.

I, like many others, were under the impression that going through a lot of credit card offers would be harmful.

And if you do it wrong, it can be.

Yet, do it right, travel hacking can help build your credit score.

My first tip is to sign up for a site like Credit Sesame, that allows you to track your credit score. You’ll then get personalized tips on how to improve your score and many other helpful features.

Next, is when you’re first starting out look for no annual fee cards.

With no annual fee cards the sign up bonuses are often a lot less. However, one factor of your credit score is the length of your credit history. By having one or two no fee cards, which you’ve kept open for a length of time, your credit score will improve.


# 5 – Don’t Be Afraid Of Cards With Annual Fees But Study The Terms

One credit card I signed up for recently was Chase Sapphire Reserve. This card comes with a $450 annual fee. (At the time I signed up it had a 100,000 bonus, now it’s 50,000).

One benefit of the card was a $300 statement credit for travel each cardmember year.

The goal is to have the rewards outweigh the annual fee.

This won’t always be the case, as everyone’s spending is different. But run the numbers yourself, to see if it does.

Compare this card to other top travel rewards credit cards.

# 6 – Sign Up For Free To Loyalty Programs To Learn About Redemption Options

If you’re looking to redeem your miles for airfare, one option would be to first look at an airline’s travel award chart.

This will tell you how much it costs in points to redeem a certain flight. For example, on American Airlines to go to Hawaii from the Contiguous 48, your options are:

  • MileSAAver Off Peak – 20,000 Points
  • MileSAAver – 22,500 Points
  • AAnytime Level 1 – 40,000 Points
  • AAnytime Level 2 – 50,000 Points

With this information, all you know is the ranges of rewards for a one-way flight. The mistake you want to avoid is assuming you can get a flight for 20,000 points for your desired date

To know the amount you’ll need and the actual flight options, you’ll want to sign up for each airlines loyalty program. This way you can see the exact amount of points needed, fees, plus actual flight times.

# 7 – Use Award Search Engines

I fly from Chicago to Fort Myers often.

I typically will fly American. If I were to book through American Airline’s loyalty program, a reduced-mileage award would cost me 25,000 points.

Instead, I book the same flight through British Airways’ Executive Club for 15,000 points. More so, both Chase Ultimate Rewards and American Express Membership Rewards allow you to transfer to British Airways’ Executive Club. This makes earning points for these flights, much easier.

There are hundreds of these little quirks to know about travel hacking.

That’s why I often start my search for flights using AwardHacker. This gives me the flights, points, and loyalty programs that are available for booking flights. Here’s what a result looks like:

Travel Hacking


# 8 – Keep Track Of Everything

Travel hacking can get a little messy.

There are deadlines for when you must meet a limited spend to get a bonus. There are then times you may want to cancel a card before an annual fee hits.

It’s important you stay organized.

While I’ve tried, I haven’t found a software that does this better then a simple spreadsheet.

Here’s a free template of how I keep track of my rewards.

I keep the current inventory of cards I have on top. Then, the bottom is for sign up bonuses I may be chasing.


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