Free flights sound too good to be true. They're not—but understanding the system requires some upfront investment. This guide covers what you actually need to know without getting lost in optimization rabbit holes.
How Airline Rewards Work
The Basic Concept
Airlines and credit cards give you "miles" or "points" for spending money. You redeem those points for flights. Simple in theory, complex in practice.
Miles vs. Points
Airline miles: Tied to specific airlines (Delta SkyMiles, United MileagePlus).
Credit card points: Flexible currencies that transfer to multiple airlines (Chase Ultimate Rewards, Amex Membership Rewards).
Key insight: Flexible points are more valuable because you can transfer them to whoever has the best award availability.
Earning Strategies
Credit Card Sign-Up Bonuses
The fastest way to accumulate points. Cards offer 50,000-100,000+ points for spending $3,000-5,000 in the first 3 months.
Example: One sign-up bonus can equal a round-trip domestic flight or one-way international in business class.
Strategy: Get 2-3 strategic cards over time (not all at once—credit score matters).
Everyday Spending
Put regular expenses on points-earning cards:
- Groceries: 3-4x points at many cards
- Restaurants: 3-4x points
- Travel: 3-5x points
- Everything else: 1-2x points
Principle: Never carry a balance. Interest wipes out all value.
Flying
Actually flying earns miles, but typically less than credit card spending unless you're a frequent flyer.
Elite status matters: Higher tiers earn bonus miles.
Airline credit cards: Often earn extra miles on that airline's flights.
Other Methods
- Shopping portals (extra points on online purchases)
- Dining programs
- Hotel transfers
- Partner promotions
Major Programs Explained
Airline Alliances
Airlines form alliances sharing rewards:
Star Alliance: United, Lufthansa, ANA, Singapore Airlines, Air Canada, etc.
Oneworld: American, British Airways, Cathay Pacific, Qantas, etc.
SkyTeam: Delta, Air France-KLM, Korean Air, etc.
Why it matters: Miles in one program can book flights on partner airlines.
Key U.S. Programs
Chase Ultimate Rewards:
- Transfer partners: United, Southwest, Hyatt, others
- Best cards: Sapphire Preferred, Sapphire Reserve
- Strength: Versatility, good transfer partners
American Express Membership Rewards:
- Transfer partners: Delta, ANA, Singapore, many others
- Best cards: Gold, Platinum
- Strength: Best international airline partners
Capital One Miles:
- Transfer or book directly at fixed rate
- Best cards: Venture X
- Strength: Simplicity, good earning
Redemption Strategies
Sweet Spots
Certain routes offer exceptional value:
Examples:
- Chase → United for domestic flights (often 12,500 miles one-way)
- Amex → ANA for business class Asia (historically excellent value)
- Capital One → Turkish for Star Alliance awards
Avoiding Bad Redemptions
Don't pay more than 1 cent/point value: If you need 50,000 points for a $300 flight, that's terrible.
Business/First often better value: Award charts sometimes make premium cabins reasonable.
Avoid cash + points: Usually poor value.
The Booking Process
- Know where and when you want to fly
- Check award availability (airline websites or tools like seats.aero)
- Transfer points to the airline with availability
- Book through that airline's website
Critical: Only transfer points when you see availability. Transfers are irreversible.
Building Your Strategy
Beginner Path
Year 1: Get one good flexible points card. Learn the basics. Book one award flight.
Year 2: Add a second card strategically. Explore transfer partners.
Year 3+: Optimize based on your travel patterns.
Card Recommendations
If you can only have one: Chase Sapphire Preferred (good earning, valuable transfers, annual fee offset by benefits).
Add later: Amex Gold (groceries, restaurants) or airline-specific card if you have loyalty.
High spender/traveler: Chase Sapphire Reserve or Amex Platinum (expensive but premium benefits).
Choosing Your Focus
Domestic focus: Chase → United/Southwest Europe focus: Amex → partners (many European options) Asia focus: Amex → ANA, Singapore, Cathay Simplicity focus: Capital One (fixed value, easy redemption)
Common Mistakes
Hoarding Points
Points devalue over time. Airlines increase redemption costs. Don't save indefinitely—use them.
Chasing Every Bonus
More cards = more complexity + credit score impact. Be strategic.
Ignoring Fees
Annual fees, foreign transaction fees, and cash advance fees eat into value.
Complex Routings
Time has value. A 4-connection routing saving $200 in fees isn't worth 20 extra hours.
Loyalty to Bad Programs
Not all programs are equal. Don't fly worse airlines just for miles.
Realistic Expectations
What's Achievable
Casual approach (1-2 cards, normal spending):
- 1-2 free domestic round trips per year
- Occasional international economy
Active approach (multiple cards, strategic spending):
- 2-4 domestic trips per year
- International business class possible
Hardcore approach (this becomes a hobby):
- Multiple international business class trips
- Near-free travel lifestyle
What It Requires
Points and miles aren't "free"—they require:
- Annual fees (often $95-550)
- Time learning and managing
- Good credit
- Spending discipline (never carry balances)
Advanced Concepts (Brief Intro)
Award Charts
Fixed prices for routes. Knowing these reveals value.
Dynamic Pricing
Some programs (Delta, United) price awards like cash fares. Harder to find value.
Stopovers and Open Jaws
Some programs allow free stopovers or flying into one city, out of another. Creates travel opportunity.
Status Matching/Challenges
Airlines sometimes match or offer accelerated paths to elite status.
Tools and Resources
Websites
- The Points Guy: News and valuations
- One Mile at a Time: Reviews and strategies
- Seats.aero: Award availability search
Apps
- AwardWallet: Track all your balances
- Award Expert: Search for award availability
- Airline apps: Check specific program availability
Getting Started Today
- Check your credit score (need 700+ for best cards)
- Assess your spending (what categories are highest?)
- Pick one starter card (Chase Sapphire Preferred if unsure)
- Meet the sign-up bonus (without spending extra)
- Book one award flight (domestic, simple)
- Decide if you want to go deeper
The goal isn't optimization for its own sake—it's funding travel you wouldn't otherwise take. Start simple. Add complexity only if it genuinely helps.
Compare flight prices and plan award redemptions with TripPlan—our AI helps you find the best use for your miles and points.
