Top Mistakes to Avoid When Booking Trips with Points

Earning points and miles can feel like winning free travel. But turning those rewards into flights and hotel stays isn’t always straightforward. One wrong move can cost you hundreds of dollars in hidden fees, missed opportunities, or even wasted points.

Whether you’re new to loyalty programs or already have a solid stash of rewards, this guide will help you identify the top mistakes to avoid when booking trips with points — and how to travel smarter because of it.

Why Booking with Points Is Different from Cash

When you use cash to book travel, you have flexibility, clear pricing, and full-service options. But with points:

• Availability can be limited
• Prices can be dynamic or seasonal
• Terms vary between programs
• Transfers may be irreversible
• Some points expire if unused

Because of these factors, planning ahead and understanding the rules becomes essential.

Mistake 1: Transferring Points Without Confirming Availability

This is by far the most common — and costly — mistake.

Why it matters: Once you transfer points (e.g., Livelo to Smiles or Amex to Flying Blue), you can’t reverse the transaction. If there’s no award space left or the price jumps, you’re stuck.

What to do instead:

• Search award space first using airline websites or tools like AwardHacker or Point.me
• Only transfer points once you’ve confirmed availability and are ready to book
• Monitor award trends for a few days if you’re flexible on dates

Mistake 2: Ignoring Transfer Bonuses

Many programs offer temporary bonuses when transferring points. For example:

• Livelo → TAP Miles&Go: often 100%
• Amex → British Airways: 30%
• Esfera → LATAM Pass: 50%

Why it matters: A 100% bonus effectively cuts your needed points in half.

What to do instead:

• Track ongoing transfer bonuses via blogs and promo calendars
• Wait for bonus windows before transferring if possible
• Stack bonuses with booking promotions (e.g., discounted redemptions)

Mistake 3: Booking Too Late

Award seats often disappear quickly, especially in premium cabins or during high season.

Why it matters: Last-minute redemptions can cost more miles — or leave you with no seats at all.

What to do instead:

• Book 6–11 months in advance when award calendars open
• Use tools like ExpertFlyer to set seat alerts
• Be flexible with dates and routes for better availability

Mistake 4: Not Understanding Dynamic Pricing

Many programs (like LATAM Pass or Delta SkyMiles) use dynamic pricing, where the number of points needed changes based on demand.

Why it matters: The same flight might cost 35,000 points one day and 90,000 the next — with no warning.

What to do instead:

• Track prices over time to spot patterns
• Use flexible date searches to compare options
• Book when you see value — dynamic pricing rarely favors waiting

Mistake 5: Booking Partner Awards on the Wrong Platform

Booking a flight on a partner airline using the wrong website can cost you more points or lead to a failed booking.

Example:
You want to fly from New York to Frankfurt on Lufthansa. Booking through United may require fewer points than booking through Lufthansa itself — or vice versa.

What to do instead:

• Compare redemption rates across different partner programs
• Learn how airline alliances work (Star Alliance, Oneworld, SkyTeam)
• Use the program with the best deal, even if it’s not the operating carrier

Mistake 6: Ignoring Taxes and Fees

While points may cover the base fare, they don’t always cover taxes, surcharges, or fees.

Examples:

• British Airways flights often carry high fuel surcharges
• Airports like London Heathrow add US$200+ in taxes
• Hotel redemptions may exclude resort fees

What to do instead:

• Always click through to the final booking screen to see total charges
• Consider alternate airports or routes with lower fees
• Use points on programs that include taxes (like Southwest or JetBlue)

Mistake 7: Not Being Logged In or Eligible

Some promos or award prices are only available to:

• Loyalty club members (Clube Smiles, TudoAzul)
• Elite status holders
• Those who received targeted offers

If you’re not logged in or part of a club, you might miss out.

What to do instead:

• Always log into your loyalty account before searching
• Subscribe to a points club during high promo periods
• Check if an offer requires activation or eligibility confirmation

Mistake 8: Booking Non-Refundable Awards Without Certainty

Points bookings can be tempting, but if your plans are not confirmed, you could lose:

• Your points (partially or fully)
• Your money (in taxes or cancellation fees)

What to do instead:

• Check cancellation policies — some programs offer free changes (e.g., Alaska, United)
• Use refundable cash bookings as a placeholder
• Book awards only when your trip is firm, or choose flexible programs

Mistake 9: Ignoring Expiration Dates

Some programs have strict expiration policies:

• Smiles miles: 3–10 years depending on source
• TudoAzul: 2 years
• Amex MR: never expires (until transferred)

What to do instead:

• Track expiration dates using a tool like AwardWallet
• Transfer only when necessary
• Renew expiring miles with small activity (e.g., buy something in the portal)

Mistake 10: Not Comparing Points to Cash

Sometimes, points redemptions seem like a deal — but aren’t.

Example:

• A flight costs 40,000 miles + $100 in fees
• Cash price is $300
• Your effective redemption rate is only $0.005 per point (low value)

What to do instead:

• Always calculate cents per point value
• Aim for redemptions that offer 1.5–2 cents per point or more
• Consider saving your points if the cash rate is low

Mistake 11: Forgetting to Earn on Redemption Flights

Some airlines (especially partner programs) let you earn miles even on award tickets if you:

• Add your frequent flyer number
• Pay taxes or fees with an eligible card
• Book a specific fare class or promotion

What to do instead:

• Always add your loyalty number, even on awards
• Check if your program allows points on redemptions
• Use partner platforms that stack benefits

Mistake 12: Using All Your Points on One Trip

Burning your entire balance on one redemption can leave you vulnerable to:

• No points left for emergencies
• Missing future transfer bonuses
• Poor redemption value if the trip isn’t optimized

What to do instead:

• Leave a small buffer in your account
• Diversify your programs and balances
• Use a mix of points and cash when needed

Mistake 13: Relying on One Program Only

Loyalty programs change their rules often. If you put all your effort into one airline or hotel group, you risk:

• Sudden devaluation
• Limited availability
• Losing access to deals

What to do instead:

• Use flexible programs like Livelo, Amex, or Chase
• Keep small balances in multiple programs
• Stay alert to promos across different ecosystems

Final Thoughts: Avoiding Mistakes Saves Points and Sanity

Booking a trip with points is a powerful way to travel better for less — but only if you do it right.

By avoiding these top mistakes when booking trips with points, you’ll maximize the value of your rewards, protect your investments, and enjoy stress-free redemptions.

The best travelers don’t just earn — they redeem wisely.