10 Points & Miles Mistakes That Cost You Money

I’ve talked to hundreds of people about their points strategies. Almost everyone is making at least one of these mistakes — even frequent travelers who think they know the game.

Here are the 10 most common (and costly) mistakes, and how to fix them.

1. Not Having a Transferable Points Strategy

The mistake: Earning points in closed-loop systems (Delta, United, Marriott) instead of transferable currencies (Chase, Amex, Capital One).

Why it matters: Airline and hotel points lock you into one program. Transferable points give you flexibility to find the best deal across multiple partners.

The fix: Prioritize Chase Ultimate Rewards, Amex Membership Rewards, Capital One Miles, and Bilt Rewards. These programs let you transfer to 10-20+ airlines and hotels. Read our transfer partners guide to understand why this matters.

2. Redeeming for Cash Back

The mistake: Cashing out points for 1¢ each (or worse, 0.5¢ through gift cards).

Why it matters: Transferable points are worth 1.5-2.5¢ each when transferred to partners. Cashing out at 1¢ means you’re leaving 50-150% of the value on the table.

The fix: Only cash out if you genuinely can’t use the points for travel. For most people, transferring to partners is far better.

Exception: The Schwab Platinum lets you cash out at 1.1¢ — still not great, but acceptable in a pinch.

3. Hoarding Points Forever

The mistake: Treating points like a savings account and never spending them.

Why it matters: Points devalue over time. Airlines add fuel surcharges, hotels increase point costs, programs change rules. The best time to use points was yesterday.

The fix: Have a plan. Book trips. Use the points. They’re meant to be spent, not hoarded.

4. Transferring Before Checking Availability

The mistake: Transferring points to an airline, then discovering there’s no award availability.

Why it matters: Transfers are one-way. Once points are in an airline program, you can’t get them back. If there’s no availability, you’re stuck.

The fix: ALWAYS search for availability BEFORE transferring. Use tools like Seats.aero, ExpertFlyer, or airline websites to confirm award seats exist.

5. Ignoring Transfer Bonuses

The mistake: Transferring points at 1:1 when a 30% bonus is available.

Why it matters: Transfer bonuses are free points. A 30% bonus on 100,000 points = 30,000 extra miles. That could be a free domestic flight.

The fix: Check current transfer bonuses before any transfer. We track active bonuses on our Transfer Bonuses page. Also check our February 2026 transfer bonus analysis to see which bonuses are actually worth using.

6. Paying Full Annual Fees Without Using Perks

The mistake: Paying $550 for the Chase Sapphire Reserve but not using the $300 travel credit, Priority Pass, or other benefits.

Why it matters: Premium cards are only worth it if you use the perks. If you’re not using them, you’re paying for nothing.

The fix:

Set calendar reminders for annual credits
Use the Priority Pass lounge access
Actually claim the credits (airline, hotel, Uber, etc.)

If you can’t use at least 50% of the perks, downgrade to a no-fee card.

7. Flying Economy on Points

The mistake: Using miles for economy flights when business class is only marginally more.

Why it matters: The value of points skyrockets in premium cabins. A $5,000 business class flight might cost 80,000 miles. That’s 6.25¢/mile! Economy on the same route might cost 40,000 miles for a $400 ticket — just 1¢/mile.

The fix: Compare cash prices across cabins. If business is significantly more expensive in cash but only 2x the miles, book business.

When economy makes sense: Short domestic flights where business is just a bigger seat.

The mistake: Getting a new credit card but failing to meet the minimum spend for the bonus.

Why it matters: Sign-up bonuses are the fastest way to earn massive amounts of points. Missing the requirement means you did the hard part (application, credit inquiry) but got none of the reward.

The fix:

Only apply when you have planned spending coming up
Use the card for ALL purchases during the bonus period
Consider pre-paying bills, buying gift cards (carefully), or timing big purchases

9. Chasing Too Many Programs

The mistake: Having points scattered across 10+ programs, none with enough for a good redemption.

Why it matters: 20,000 points here and 15,000 there equals zero value. You need concentration to actually book trips.

The fix: Pick 2-3 programs and focus. For most people:

Chase Ultimate Rewards (flights + Hyatt hotels)
Amex Membership Rewards (backup + different partners)
One airline if you’re loyal (AA, United, Delta)

See our best credit cards for 2026 for the optimal card setup.

10. Not Reading the Fine Print on Transfer Bonuses

The mistake: Chasing a “50% transfer bonus to Marriott!” without understanding the math.

Why it matters: Some bonuses look great but aren’t. Marriott points are worth ~0.7¢ each. Even with a 50% bonus, you’re getting less value than keeping the Chase points (worth ~2¢).

Example:

100,000 Chase points = ~$2,000 value via Hyatt
100,000 Chase → Marriott with 50% bonus = 150,000 Marriott = ~$1,050 value

The “bonus” actually destroyed value.

The fix: Always calculate the cents-per-point value AFTER the bonus. If it’s still below 1.5¢, skip it.

Bonus Mistake: Not Using a Points Calculator

Seriously. Before every redemption, calculate your cents-per-point. If it’s below 1.5¢, you can probably do better.

Use our Points Calculator to check any redemption in seconds.

Summary

The theme here is intentionality. The people who get the most value from points:

Earn strategically in transferable programs
Search before transferring to confirm availability
Calculate value before every redemption
Use their points instead of hoarding
Pay attention to bonuses and perks

Avoid these 10 mistakes, and you’ll be ahead of 95% of points enthusiasts.

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Made one of these mistakes? We’ve all been there. Share your story in the comments!