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 from Chicago to Buenos Aires with a British Airways 100,000 point offer.

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.

Now with two kids, I’m traveling less. Therefore, travel hacking has turned into a combination of:

  • Travel hacks that save money
  • Making money with often ridiculous credit card signup bonus offers

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/make a good amount of money.

  • $2,000 in cash 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’s no doubt I find for the 10-15 hours a year I invest in travel hacking well worth the effort.

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

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. Balance transfer fee is 5% 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.

For example, between October 1st and December 31st, I’ll earn 5% cash back on all Walmart purchases. Having Walmart as a rotating category has been great as we’ve been using Walmart Grocery. (Get $10 off your first online order with this link).

Learn more about the Chase Freedom Card

# 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 (my referral link) card earns 1.5% cash back for all purchases.

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

If your goal is to maximize your cash back, you may want to just get a 2% cash back card. One such offer out right now is the Citi Double Cash, where you earn 1 point per dollar when you spend and 1 point when you pay.

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# 3 – Sign Up For Birch Finance To Maximize Your Rewards

Bonus category spending, cash back vs. points, reward programs…. if all this is sounding foreign to you, I recommend signing up for the free app Birch.

Birch helps you maximize your earnings by letting you know the best card in your wallet to use on every purchase.

The free app has many different features. One aspect though I like is the weekly “This Week’s Missed Rewards” email I get.


This app is a great way to teach yourself (or your spouse) to maximize your points. It provides the consistent feedback needed, with no effort from you.

Learn more about Birch.

# 4 – 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).

# 5 – Know Your Credit Score

My # 1 reason for not playing this game sooner was 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.

Credit Sesame Quick Summary

  • Get your credit score for free in under 90 seconds
  • Get personalized tips on how to improve your score
  • Highly rated app with a rating of 4.3 and 21,000+ votes
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    No credit card needed & it won't impact your score


# 6 – 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 calendar year (now it’s cardmember year, so this option is not available).

Say you signed up for the card in December, and used your $300 statement credit for travel then. In January, your $300 annual statement credit would refresh. Therefore, you could have received $600 in credits (plus 100,000 in points) for owning the card for a few months.

This benefit far outweighs the $450 annual fee.

While Chase changed its policy and this option is no longer available — what’s important is to study and know what you’re getting for the annual fee.

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.

# 7 – 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.

# 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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8 Travel hacks that save money. Discover 8 different ways to maximize your credit card points to travel for less (A LOT LESS). 

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