Travel Hacking 101: How to Book Your First Award Flight
Travel Hacking 101: A beginner’s guide to using points and miles for airfare—without the overwhelm.
Do you have points and don’t know what to do with them? This guide is for you! I have been using points and miles for over 20 years for free flights. This year alone, I booked over 30 round-trip tickets for my family. Check out these important steps to book free flights.
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Step 1: Know Your Points
Start by identifying what kind of points you have:
Credit card points (e.g., Chase Ultimate Rewards, Amex Membership Rewards)
Airline miles (e.g., Delta SkyMiles, United MileagePlus)
Hotel points (not for flights, but sometimes transferable)
💡 If you have flexible points (like Chase or Amex), you can transfer them to airline partners for better value. Check out my credit card transfer guide -> Credit Card Transfer Partners — No Point Left Behind
Step 2: Pick a Destination + Dates
Award availability depends on:
Where you’re going
When you’re traveling
How many seats you need
Tip: Be flexible with dates and airports. Consider flying midweek or using nearby cities.
Step 3: Search for Award Availability
Use these tools to search:
Point.me – Best for beginners; shows availability across multiple airlines
Airline websites – Search directly (e.g., United.com, AA.com)
Partner sites – Sometimes better than the airline you want to fly (e.g., book Air France flights via Flying Blue)
📌 Example: For our Toronto trip, we used Air France miles to book WestJet flights—thanks to a partner redemption sweet spot. Read about how I booked our trip -> Weekend in Toronto On Points
Step 4: Transfer Points (If Needed)
Once you find availability:
Log into your credit card portal (Chase, Amex, etc.)
Transfer points to the airline program
Transfers are usually instant—but double-check before you move them
⚠️ Transfers are one-way and irreversible. Confirm availability before transferring. Not sure who the different transfer travel partners are for each card. Check out these posts:
Step 5: Book your Flight -
Go to the airline’s website
Log in and search for your flight again
Select the award flight and complete the booking
Pay any taxes and fees (usually $5–$100 per ticket)
✈️ Woohoo, you did it!
Bonus Tips
Start with one-way flights to learn the process
Use miles for domestic flights to avoid high taxes
Book early—award seats can disappear fast
Add frequent flyer numbers to earn elite credit (if applicable)
Ready to Book?
Check out our “How I Booked It” series for real-life examples: → Princess Cruises Greece dream |Big savings Princess Cruise Alaska | European Family Vacation Points and Miles
Let’s Travel Hack Together
If you enjoy learning how we travel as a family using points, miles, and smart credit card strategies, I’d love for you to follow along:
