How to Maximize Travel Rewards: Tips for Earning Free Flights and Hotel Stays
Please note this post contains affiliate links and I may receive bonus points should you decide to apply and be approved for any of these cards.
We’re incredibly lucky to travel often. For the first decade of my career, I was always on the move—flying frequently and constantly on the road. Add in a family in Canada and our love for exploring new places, it's clear that travel is a big part of our lives. While travel can be expensive, learning how to maximize points and rewards can stretch your budget so much further. For instance, we were able to cover all 10 days of hotel rooms and one flight to Italy with rewards points.
1. Decide Who You’ll Be Loyal To
When it comes to airlines and hotel chains, there are pros and cons to every major brand. However, building loyalty with one or two companies can make a huge difference in the long run. Not only will you get perks like priority customer service, upgrades, and faster point accumulation, but staying loyal also increases the likelihood of earning valuable rewards.
Personally, we stick with Delta for flights and Hilton for hotels. My loyalty to Delta started back in college when they offered the best flights to Alberta, Canada. However, over the years I’ve found that their customer service and overall flight experience is what I love most. While I love Southwest and used to fly them frequently in Kansas City, we now try to stay with Delta since our local airport no longer services Southwest. As for Hilton, we’ve enjoyed their diverse range of properties, but if you're traveling through smaller towns more often, IHG (Holiday Inn) might be a better choice.
2. Get the Right Credit Card
Let’s be real—relying solely on rewards programs isn’t going to cut it if you want to travel for free. The key to maximizing your points is pairing your loyalty with the right credit card. A good travel rewards card will not only earn points for flights and hotel stays but also your everyday purchases.
For example, on a recent stay at a Hilton hotel, we earned 3,870 points for one night (1,025 base points, 1,025 summer bonus, and 1,820 bonus points because of my elite status). I then received an additional 1,854 bonus points because I paid for the room using my Hilton credit card. The total cost for a room like that is around 29,000 points during off-peak times, so I need to repeat this process about five times to earn a free stay. But when using a Hilton credit card the free rooms are going to happen much faster because of the next strategy.
3. Put Everything on the Credit Card—and Pay It Off
Let me be clear: Only charge what you can afford to pay off immediately. There are no rewards worth the high interest rates that come with carrying a balance. We put every single purchase—whether business or personal—on our points-earning credit cards. But here's the catch: I pay off the balance multiple times a month. I can’t stand seeing a large balance at the end of the month, and it helps us stay on top of our finances. By strategically using our business and personal cards, we usually score 2-3 free flights and several hotel nights each year.
Pro Tip: I travel more so whenever we purchase a flight it goes in my name, and we use all the free flights for Jon (you don’t receive points on a free flight). Similarly, when booking a hotel they are all under my rewards number. This helps us build the most points under one person instead of having them split up and then needing to transfer points.
4. What Rewards Credit Cards Should You Sign Up For?
Which credit cards should you sign up for?
Delta Platinum Skymiles American Express: I’ve had this card for over 10 years, and it’s a solid choice for frequent travelers. Despite its $350 annual fee, the benefits far outweigh the costs. Perks include:
First checked bag free
Companion pass (essentially buy one flight, get another free)
Accelerated earning toward airline status (which means upgrades and bonus miles)
This card also helps us build points faster, making it easier to redeem for free flights.
Hilton Honors American Express Surpass Card: This card is a newer addition to our wallet, mainly for business travel. The sign-up bonus was too good to pass up, offering us several free nights at Hilton properties. Plus, it automatically grants Gold status in Hilton Honors, which unlocks better perks like free breakfast and room upgrades. After spending $15,000 in a calendar year, you earn a free night at any Hilton property.
A great example of this card’s value: We used our free night certificate to stay at the Washington D.C. Waldorf Astoria on the Fourth of July—normally a $950 room—for FREE! And the best part? This card has no annual fee.
Hilton Honors American Express: This card is another we’ve had for years, and it’s great for earning Hilton Honors points. It grants you Silver status with Hilton Honors. Leading up to Italy we focused on using this card to get a few more nights of hotels covered. The Hilton Honors American Express Surpass Card mentioned above has much better benefits (I am not sure why we didn’t get this one initially, maybe it wasn’t around then?)
I am not afraid to add new credit cards and the next time we decide to add a personal card we’ll likely get the Surpass and phase out this card.
The fanciest dessert I have ever had was at the Waldorf Astoria in Washington D.C.
Good to Know: While American Express is accepted nearly everywhere, there are still some small businesses—especially in U.S. rural areas or towns around Sorrento, Italy—that don’t take it. We always carry a backup MasterCard just in case. That said, when it comes to customer service, American Express has been hands-down the best, especially when dealing with fraud and replacing lost cards.
Final Thoughts: Travel Smart, Travel More
Maximizing travel rewards is all about strategy. By aligning yourself with the right airlines and hotels, using the best credit cards, and paying off balances regularly, you can unlock incredible perks. The more you put into the system, the faster you’ll earn points that translate into free flights and hotel stays. Happy travels!