How to Travel Hack Your Dream Vacation
Disclaimer: this post contains affiliate links to products I personally use or highly recommend
The Art of Travel Hacking
Imagine lounging on a tropical beach, sipping from a coconut with a little umbrella in it, or wandering through the historic streets of a bustling new city...
Now, imagine doing it all for a fraction of the expected cost… that's my favorite part :)
Welcome to the world of travel hacking, where through a mix of strategic tools, patience, and a few lesser-known tips you can unlock travel experiences saving thousands on your way. In fact, just this past week I saved over $1,000 on a last-minute trip to Puerto Rico through a mix of credit card reward points, cash-back programs, and hotel loyalty perks.
Check out the top travel hacks below that you can use to plan your next dream vacation.
Travel Hack 1: Master Rewards Cards
While I’ll get into the lesser-known hacks in just a bit (see Hack No. 2), probably one of the most well-known strategies is using credit card rewards, not just for perks and points, but all different ways depending on your needs. While you should never get a credit card if you're not able to pay your balances off in full every month, when used responsibly, they can be your ticket to free flights, accommodations, and more. Plus, you can even double or triple the benefits with cash-back programs and shopping portals (more on this later).
Understand Reward Structures: Different cards offer different types of rewards ranging from free flights and hotels to cash-back and experiences. While some provide miles that can be redeemed with particular airlines, others offer points that can be converted into whatever suits your needs or even other vendors. Keep in mind your points may be worth more when transferred to particular vendors. In addition, there are also cash-back cards to put a portion of your spending back into your pocket — a versatile option for any traveler.
Buy-1-Get-1 Free Flights: While I've been a big fan of the Chase Sapphire Rewards card for many years thanks to big perks like complimentary lounge access, the ability to use points for 50% more when applied to travel, or pay myself back for everyday purchases, my current favorite is the Southwest Rapid Rewards card because of the coveted Companion Pass.
Let me tell you something… if you travel with a companion, whether that’s a partner, bestie, child, or family member, the Southwest Companion Pass is a game changer.
With the Southwest Companion Pass, you can get buy-one-get-one free flights for you and a companion, from any airport Southwest flies, with no blackout dates. NONE. Did I mention it’s not even limited to one companion? You can change your companion up to 4 times a year.
What's the catch? While the Companion Pass is only offered when you sign up for a Rapid Reward Card during certain times of the year, the requirements to renew it after that first calendar year are difficult (in my opinion). That said, when and if you do get it, you can easily save thousands if you frequently travel for two. Plus, you gain additional points on the card you can use like other rewards programs to redeem for free flights, hotels, etc. even if you don’t re-qualify for the Companion Pass after year 1.
Want Buy-One-Get-One free flights?
Sign up for any Southwest Rapid Rewards credit card using my referral link by 3/10/2024 and get a free Companion Pass through 2/28/2025 for BOGO flights through 2/28/2025 PLUS an extra 30,000 points when you spend 4,000 in the first 3 months.
Sign-up Bonuses and Offers: Aside from Southwest’s crazy deal, the most lucrative aspect of reward cards is usually the sign-up bonus. These bonuses can be substantial, providing enough miles or points for a round-trip flight or a luxurious hotel stay off the bat. The key is to meet the spending requirement within the specified period assuming you can pay off your balance in full every month. If you’re not confident you’ll be able to pay the card off immediately, stick to cash-back programs and other travel hacks below to take your dream vacation at an affordable price.
Travel Hack 2: CashbackMonitor
Not all points-earning strategies involve a credit card. One of my favorite travel and cash-back hacks of all time is CashbackMonitor.com, a game-changer for making any online purchase.
What is CashbackMonitor.com?: Cashbackmonitor.com is a website that compares the cashback and reward points offered by different shopping portals, ensuring you get the best deal for your online shopping across HUNDREDS of vendors. Let's say, for example, you’re looking at hotels at Booking.com or Marriott because you’re part of their rewards program. You can easily type in the store you want to shop from — Target, Nordstrom, whatever— and see where you'll get the most cash back from. You'll also see which credit cards might be offering extra points at that particular merchant. It’s like the golden ticket of cashback programs.
Below is an example using Booking.com, where you can see RetailMeNot offers the highest cashback at 20% (up to $50) at the time of this search.
So before you book travel or make a big purchase anywhere (not just travel sights) make sure to check CashbackMonitor to save as much as possible!
Living the dream eating a beef pastelillo on Isla Verde Beach in Puerto Rico
How I Saved $1,000+ on a Weekend Trip to Puerto Rico
I saved $600+ using my Southwest Rapid Reward Points on a last-minute flight
I saved $300+ using Google to find the best hotel deal with Marriott, which I got an extra 10% off using a promo code
I got $40 (4%) cash back via RetailMeNot using CashbackMonitor.com
As a Marriot Bonvoy rewards member, I was upgraded to a suite complete with kitchen and dining room: estimated savings, $225 total
Marriot also had a promotion going on, so I got 3 bonus nights towards Silver Elite status which will pay off at a future date
Lastly, I plan on using points from Chase Rewards to pay myself back for portions of my trip. While the points would be worth more if I used them directly towards flights or travel, the pay-yourself-back option is always nice to have!
Travel Hack 3: Stack Rewards Using Portals and Offers
Did you know most major credit card programs also have monthly offers and shopping portals where you can earn extra points or cash back to use towards your next vacation? Some examples of popular card shopping portals include Shop Through Chase, Citi Bonus Cash Center, and Southwest Rapid Rewards Shopping, making every purchase an opportunity to double or triple up on travel rewards — but that’s not all. Most banks and financial institutions also offer monthly offers in addition to any shopping programs affiliated with their credit cards.
By using a rewards card, through a portal and/or activating special offers, you can easily save hundreds on your next dream vacation. For example, Chase and Amex (among others) both provide monthly offers of up to 20% back for select stores that users will need to activate every month. Unfortunately, as these offers are often specific to the individual, there is no way to easily check offers across institutions. That said, you can usually sign up for notifications from your bank or credit card company to be notified when new offers are available to use on things like travel, but also shopping groceries, and other services.
Travel Hack 4: Use Comparison Sites
With the right tools, finding affordable travel options becomes much easier. Travel comparison sites like Google Flights, Kayak, and Booking.com are three of my favorites when it comes to booking travel.
Google Flights: Google Flights allows you to explore destinations based on your budget and travel dates, showing you the best times to fly. Its price tracking feature alerts you when prices drop, helping you book at just the right moment.
Kayak’s Hacker Fares: Kayak offers "Hacker Fares," which are combinations of one-way tickets that often cost less than a round-trip ticket with a single airline. This can lead to significant savings, especially on international flights.
Booking.com: While there are comparable sights to Booking.com like Priceline or Expedia, I tend to find their platform the most user friendly, their rates are always reasonable, and I appreciate their “Genius” discounts of 10% or more once you’ve booked a few trips through their platform. To stack rewards, I’ll use cash back programs on top of Booking to make sure I get the most bang for my buck.
Keep in mind most platforms also allow you to set price alerts for specific routes, and if you’re flexible, you can usually save even more.
Travel Hack 5: Think Outside the Box
Beyond credit cards and flight comparison tools, here are a few extra travel hacks to help you save on your next vacation.
Incognito Mode for Searching: Prices can increase based on your search history. Using incognito mode in your browser can sometimes reveal cheaper prices for flights and hotels.
The 24-Hour Rule: Many airlines offer a 24-hour cancellation policy; this is particularly true thanks to new U.S. Department of Transportation regulations. This means you can book a flight to secure a good price and have 24 hours to cancel for a full refund if your plans change, or you find something cheaper!
Loyalty Programs Beyond Airlines and Hotels: Don't overlook car rental and dining loyalty programs. These can offer valuable perks and rewards that add up, especially for frequent travelers.
Conclusion: Your Ticket to Travel Awaits!
Travel hacking isn't just for the ultra-organized or finance-gurus; it's for anyone willing to spend a bit of time learning the ropes. By mastering reward credit cards, leveraging tools like CashbackMonitor.com, and utilizing platforms like Google Flights and Kayak, your dream vacation can be closer than you think!
Remember, the world is a big place, and with a bit of creativity and strategic planning, exploring it doesn't have to empty your bank account. Start applying these travel hacking strategies today and I can’t wait to see where you travel to next!
