Award Booking Mistakes I Made (And How You Can Avoid Them)
Booking award travel can feel like unlocking a secret level of travel hacking—but it’s not without its traps. Over the years, I’ve made just about every mistake you can imagine when using points and miles. In this post, I’ll share some of my biggest award booking mistakes so you don’t have to repeat them.
Whether you’re planning your first award redemption or have booked dozens of flights using miles, these lessons could save you thousands of points—and hours of frustration.
🔍 Mistake #1: Not Checking Partner Airlines for Better Availability
I once spent 80,000 United miles on a one-way business class ticket to Europe. It felt like a win at the time—until I realized I could have booked the exact same flight through Air Canada Aeroplan for 60,000 points.
Lesson:
Always check across multiple partner airline programs. Most airline alliances let you book the same flights through different programs, often at drastically different mileage rates.
🗓️ Mistake #2: Booking With Fixed Dates Too Early
I locked in an award ticket months in advance, only to see significantly better flights open up later. Rebooking would have cost me change fees and additional points.
Lesson:
Award availability often fluctuates. If your dates are flexible, you may find much better options by waiting and tracking award space—especially close to departure or right when the schedule opens (~330 days out). However, if you find a flight that you know you’ll be happy with, book it immediately! Award space can disappear quickly, and there’s no guarantee it will remain available so don’t make that award booking mistake either.
❌ Mistake #3: Using Miles for Cheap Domestic Flights
I redeemed 12,500 miles for a $150 domestic flight because it “felt free.” But when I later saw how far those points could go on international routes or premium cabins, I regretted it.
Lesson:
Save your points for high-value redemptions. Try to aim for 2+ cents per point. If the cash price is relatively low, it’s often better to pay with money and save your miles for more expensive trips.
🔄 Mistake #4: Ignoring Transfer Bonuses
I transferred Chase Ultimate Rewards to Virgin Atlantic to book a Delta flight—when there was a 30% transfer bonus available through Amex Express Membership Rewards. Had I taken the time to check, I could’ve used fewer points for the same flight.
Lesson:
One of the easiest ways to stretch your points further is by taking advantage of transfer bonuses offered by programs like Chase Ultimate Rewards, Amex Membership Rewards, and Citi ThankYou Points. These bonuses can boost your mileage by 20–40%, giving you significantly more value on the same redemption.
Before transferring points, always check current promotions.
We maintain an up-to-date list of the latest bonuses here: 🔗 Current Transfer Bonuses »
Bookmark that page—it could save you thousands of points.
🧭 Mistake #5: Not Understanding Stopovers vs. Open-Jaws
I once tried to book a complex multi-stop trip without fully understanding the rules of the airline program I was using. I ended up wasting points on inefficient routing and paid extra taxes for unnecessary connections.
Lesson:
Always read the fine print. Programs differ widely in how they handle stopovers, open-jaws, and multi-city itineraries. Some allow you to stop in multiple cities for no extra cost—others don’t allow any stopovers at all.
😵 Mistake #6: Not Saving Points for High-Value Redemptions
I used most of my Membership Rewards points on short domestic economy flights. They served a purpose, but I missed the opportunity to fly in business or first class—experiences I had originally hoped for.
Lesson:
Premium cabins generally offer more value per point. That said, don’t hoard points forever—they lose value over time due to devaluations. Strike a balance between saving for high-value redemptions and using your points before they become less valuable.
💸 Mistake #7: Ignoring Fuel Surcharges
I once used points to book a flight on a major European airline, thrilled to score a “free” flight—until I got hit with nearly $800 in taxes and carrier-imposed fees.
Lesson:
Surcharges can completely ruin a good redemption. Programs like Air Canada Aeroplan, Avianca LifeMiles, and United MileagePlus generally avoid passing on high surcharges, even when booking partners like Lufthansa or Swiss.
✅ How to Avoid These Award Booking Mistakes
| ✅ Do This | ❌ Not That |
|---|---|
| Compare partner programs | Book blindly through your main airline |
| Use flexible dates | Lock in fixed dates too early |
| Save for premium redemptions | Burn points on low-value economy flights |
| Wait for transfer bonuses | Transfer without checking promos |
| Learn program rules | Assume they all work the same |
| Check surcharges | Assume all redemptions are “free” |
Final Thoughts
Award booking is both an art and a science. It’s easy to assume that using miles is always the better option—but like cash, they need to be used wisely. If you’re unsure how to make the most of your points, or just want help finding the best available flights, check out our 👉Award Booking Service. We’ll help you unlock your points’ full potential—without the headaches.
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