We tried it: Using points and miles to book travel (without being experts) / 84
If you've ever fallen down the travel rewards rabbit hole, you've probably come away feeling like there's a "right" way to use credit card points.
Transfer partners. Sign-up bonuses. Maximizing every redemption.
While those strategies can absolutely help you stretch your points further, they can also make it feel like you need to become a travel hacking expert before you're allowed to book a trip.
In reality? You don't.
This summer, we both redeemed credit card points for trips we were genuinely excited about — and neither of us did it in the most optimized way. Instead of chasing the perfect redemption, we chose the option that helped us save money, reduce financial stress, and support our current goals.
Episode highlights
[00:00] Why we're confessing our "imperfect" approach to using credit card points
[02:50] Breaking down Cass's last-minute trip to Toronto—flights, hotels, and how points covered nearly $2,000 in travel
[07:15] Why Cassidy chose to redeem points through the Chase Travel portal, even though it's not the strategy most travel experts recommend
[09:45] How Emily thought about buying a cross-country flight to Seattle while balancing other financial priorities
[11:20] Using Google Flights, Points Path, and airline rewards programs to compare cash versus points
[14:10] Why Emily intentionally ignored advice to pay cash and save points for later
[15:20] How we earned our travel rewards through Chase, United, and Delta credit cards
[17:00] What we're still learning about transfer partners, airline loyalty, and maximizing points
[18:00] Why the "best" redemption depends on your personal financial goals, not someone else's spreadsheet
[19:10] Our biggest takeaway: using your points to reduce financial stress is a win, even if it isn't perfectly optimized
The best redemption is the one you'll actually use
There's no shortage of advice online about maximizing the value of your points. (Trust us, we’ve spent a lot of time digging through it.) But it's easy to forget that the ultimate purpose of travel rewards isn't to optimize every last detail — it's to help you travel in a way that supports your life.
For example, we were both recently booking trips with fixed dates and specific destinations. We weren't searching for the cheapest award flight to anywhere in the world. We were booking travel for events and experiences that mattered.
That reality changed the equation.
Instead of asking, "How can I get the highest cents-per-point value?" we asked:
Will using points help me avoid spending cash I'd rather save?
Does this trip fit my financial goals right now?
Is the simpler booking option worth it to me?
For us, the answer was yes.
Cassidy's Toronto trip: Choosing convenience over perfect optimization
Cassidy booked a last-minute trip to Toronto using Chase Ultimate Rewards points.
She redeemed points for:
A round-trip flight that would have cost about $773 in cash.
A two-night hotel stay that would have cost nearly $1,200 because of high demand during local events.
Altogether, using points covered almost $2,000 in travel expenses.
Could those points potentially have gone further through transfer partners?
Probably.
Did that matter as much as avoiding a large out-of-pocket expense during a season when discretionary income felt limited?
Not at all.
Many travel rewards enthusiasts might be shocked to learn that Cass booked everything through the Chase Travel portal simply because it was the method she already understood.
Rather than spending hours researching advanced strategies, she chose the option that felt manageable.
There's value in that, too.
Emily's Seattle trip: When saving cash matters more than maximizing points
Emily's plan looked a little different.
She and her husband are traveling to Seattle for a wedding before extending the trip to spend time with friends and go camping.
Before booking, she compared several options. This meant using:
Google Flights to monitor airfare
The Points Path browser extension to compare cash prices with points redemptions
Her United MileagePlus account to evaluate booking directly with the airline
Points Path consistently recommended paying cash and saving the points for another trip — and objectively, that may have been the better value.
But it wasn't the better decision for Emily.
Because she and her husband are actively saving for a house, using points allowed them to keep more cash available for a financial goal that mattered more than squeezing every possible dollar of value from their rewards.
They redeemed 65,200 United miles (plus taxes) for two round-trip tickets — an outcome that felt aligned with their priorities, even if it wasn't the mathematically perfect redemption.
Travel rewards don't have to be all or nothing
One thing we both noticed is that travel rewards become much easier to use the longer you stick with a system.
Emily has accumulated United miles by consistently flying United and using her United credit card.
Cassidy has built balances with both Chase Ultimate Rewards and Delta SkyMiles through regular spending and credit card sign-up bonuses.
Still, neither of us considers ourselves travel hacking experts.
We're still learning about:
Transfer partners
Airline alliances
Bonus transfer promotions
Maximizing redemption values
But that doesn’t mean we’re waiting to become experts to start taking advantage of points and miles.
Your financial goals should drive your travel decisions
One of the biggest lessons from this experience is that the "best" way to use credit card points depends entirely on your own situation.
If paying cash for a trip won't affect your finances, maybe it makes sense to save your points for a future redemption.
But if using points allows you to:
Protect your emergency fund
Keep saving toward a house
Avoid dipping into discretionary spending
Travel without adding financial stress
...then that's a successful redemption, too.
Travel rewards are a tool, not a scorecard. Remember that next time you feel paralyzed by an expert’s strategy. And focus on using your money (and your points) in a way that supports your goals — whatever they may be.
TL;DR
Your travel rewards don't have to be perfectly optimized to provide real value.
Using points instead of cash can support larger financial goals like saving for a home or preserving your emergency fund.
Tools like Google Flights and Points Path can help you compare your options, but they don't get to decide your priorities.
Consistently earning points through cards and airline loyalty programs can make future travel more affordable.
A redemption that reduces financial stress is still a great redemption, even if it isn't the most optimized one.
✨ Resources ✨
Points & miles 101 with Ross Alcorn: Turn your credit card rewards into free travel / 52
The freedom formula: How to travel, build a career, and save money with Caroline Lupini / 53
This content is for educational purposes only and should not be considered personalized financial, legal, or tax advice.
