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Hey, it’s Jeffrey, back again!
If you’ve opened a travel credit card, flown with points, or joined a frequent flyer program “just in case,” chances are…you’ve got miles or points sitting idle.
But when’s the last time you checked?
This week, I explored how to use AI and smart apps to:
✅ Track points across all your cards and accounts
✅ Get alerts before anything expires
✅ Decide when to use points vs. pay in cash
✅ Search for award flights faster
You don’t need to be a travel rewards expert — you just need to avoid wasting what you’ve already earned.
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📬 In this email:
In today’s Money Meets AI edition, we look at:
📦 Step 1: Track Your Points Automatically (and Get Alerts Before They Expire)
💰 Step 2: Ask AI “Should I Use Points or Cash?”
🔎 Step 3: Find Flights with PointsYeah
🛠️ Other Tools to Check Out
🔁 What to Do Now
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THIS WEEK’S TESTED TOOLS
📦 Step 1: Track Your Points Automatically (and Get Alerts Before They Expire)
The first step to actually using your points is remembering you have them. Tools like AwardWallet and MaxRewards automatically track your balances and flag expiration dates.
Just connect your travel programs (airlines, hotels, etc.), and these apps will monitor your balances and expiration dates in the background.
💡 Bonus: AwardWallet can even send email or push alerts when your points are about to expire — so you have time to act.
Here’s how MaxRewards looks for credit card tracking:
MaxRewards offers a free version and a premium version that’s available on a sliding scale and costs a minimum of $8 a month, billed annually, at $96 per year.
And Award Wallet looks like this:
AwardWallet offers a free version and a premium version ($49.99/year)
🤖 Step 2: Ask AI “Should I Use Points or Cash?”
Even when you remember you have points, it’s not always clear if using them is worth it. This is because points are valued differently for different miles or points programs.
And point values can change over time.
ChatGPT can help you decide. Just ask:
I found flights to Lisbon for $800 or 65,000 miles + $11.20 in taxes. Should I use points or pay cash?
It’ll calculate the cents-per-point value, compare it to benchmarks (e.g., 1.5¢ for Chase Ultimate Rewards), and even ask about your travel plans or how often you use those points.
💡 Following up on its prompt for more info, I let it know these are Chase Ultimate Rewards points, and it gave me a more detailed recommendation. Here’s a sample of what it told me, including the value per point and a recommendation:
🔎 Step 3: Find Flights with PointsYeah
Best for: Making smarter purchases and avoiding false “discounts”
PointsYeah is like Google Flights, but for award travel. Instead of showing you flights in cash, it shows you the cost in points.
You plug in where you want to go, and it scans multiple airlines and point programs to show where you can book with your rewards.
It supports programs like:
United, American, Delta, Alaska
Transfer partners (Chase, Amex, Citi, Capital One)
And more
You can even filter by the lowest points required or the best flights.
Here’s the best I found when searching for nonstop flights on my itinerary above. PointsYeah shows me I can transfer 80,000 points from AMEX to Delta to book this flight.
If I don’t mind one stop, I can get a much better deal with more points options too:
What Didn’t Work So Well
I initially found the PointsYeah interface a bit intimidating, but it was easy once I got used to it.
Most tools today require creating an account. Not a huge deal, but it is not exactly my preference.
🛠️ Other Tools to Check Out
Other tools I came across but didn’t do a deep dive into for this newsletter:
The Points Guy app – Offers personalized travel tips and redemption ideas
Point.me – Searches award availability across 30+ airline programs
🎯What to Do Now
✅ Connect your accounts to AwardWallet or MaxRewards
✈️ Search for award flights with PointsYeah
🤖 Ask ChatGPT if you should use miles or cash
🕑 Set an annual calendar reminder to review your balances
PS—I’d love to hear your other feedback or suggestions. Just hit reply — I read every email!
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One quick note: This newsletter is for educational purposes only and does not constitute financial advice. I’m not a financial advisor — just someone sharing ideas and tools I’ve found useful. Use what works for you, skip what doesn’t, and always do your own research before making financial decisions and using the tools shared in this newsletter.