The 5 Biggest Mistakes People Make When Redeeming Travel Points
- Pinot & Points
- Oct 26
- 3 min read
(and how to never make them again)
Earning points is the easy part — redeeming them smartly is where the real magic (and upgrades) happen.
After years of planning luxury trips on points, I’ve noticed that even savvy travelers make a few common missteps that can cost them thousands of points - or the business-class seat they’ve been dreaming of.
Let’s fix that. Here are the top five mistakes I see, and how to avoid them so your next redemption feels as good as that pre-flight glass of Pinot. 🍷
1️⃣ Redeeming Through a Travel Portal Without Checking Other Options
Travel portals like Chase Ultimate Rewards or Amex Travel make it so tempting to click “book” — everything’s right there in one place.
But here’s the problem: the value per point is often lower than what you’d get by transferring your points directly to an airline or hotel partner.
For example, instead of redeeming 200,000 points through the portal, you might transfer to Air France Flying Blue and book a similar business-class seat for 80,000. Same destination, 120,000 points saved.
Pinot Pro Tip: Always compare portal pricing against a partner transfer before you redeem. Those few extra minutes can unlock first-class value for economy prices.
2️⃣ Not Being Flexible With Travel Dates
Award pricing fluctuates - sometimes dramatically.
The same route could be 60,000 points on a Tuesday but 150,000 on a Friday. Flexibility is the difference between “we got lucky” and “we got upgraded.”
If your schedule allows, search a few days before and after your ideal date. Tools like Google Flights, ExpertFlyer, Gondola AI and some airline and hotel calendars show flexible award views.
Pinot Pro Tip: Move your trip by just one day and you could save enough points for your next weekend getaway.
3️⃣ Ignoring Repositioning Flights
This is one of the most overlooked strategies in the points world.
Can’t find a good award seat from your hometown? Look from a different major hub instead — JFK, ORD, LAX, DFW, or ATL. Then, book a cheap positioning flight to get yourself there.
Yes, it adds one small hop, but it can open up premium award availability you’d otherwise never see.
Pinot Pro Tip: When you see “no seats available,” ask: from where? That one change can unlock the exact redemption you’ve been chasing.
4️⃣ Forgetting About Transfer Bonuses
If there’s one phrase that should make every points collector perk up, it’s transfer bonus.
Amex, Chase, Bilt and Citi often run 20%–30% bonuses to specific partners (like Flying Blue or Virgin Atlantic). That means a 100,000-point transfer could land as 120,000 points in your airline account — enough for a serious upgrade.
And here’s the best part: these bonuses happen several times a year.
Pinot Pro Tip: Don’t transfer your points until a bonus hits and you’ve confirmed award availability. That’s how you stretch your stash the furthest.
5️⃣ Not Paying Off Your Credit Card in Full Each Month
It’s the least glamorous topic, but the most important.
If you’re carrying a balance, the interest you pay wipes out the value of your rewards — and then some. Points are powerful, but only if you’re playing from a place of financial control.
Pinot Pro Tip: Treat points like a bonus, not a bailout. Pay off your cards in full every month so your rewards stay truly rewarding.
🍷 The Pinot Edit Takeaway
Redeeming points well is equal parts art and timing — and the best redemptions go to the travelers who slow down, compare, and plan with intention.
Every mistake on this list can be fixed with one mindset shift: think like a strategist, not a spender.
Save this post, share it with your travel-loving friend, and let’s make sure your next redemption feels like a luxury — not a lesson.
Follow @Pinot_And_Points on Instagram for weekly travel strategies, redemption inspo, and luxury family travel tips that turn points into paradise. 🌍