5 Amazing Trips You Can Book with Points (Instead of Cash)
Imagine this.
You’re scrolling through flight prices and your jaw drops… You see $1,200 for a flight to Europe, $600 for a family trip to Disney, or $7,000 for business class to Asia. And these prices are PER PERSON. It feels out of reach, right?
Now imagine booking those exact same trips for just a fraction of the cost, and sometimes even free, simply by using credit card points and miles. That’s the magic of travel hacking.
In this post, I’ll show you five amazing trips you can book with points instead of cash. These are real, beginner-friendly examples that prove you don’t need a trust fund or endless vacation days to travel the world.
And if you’re brand new to all this, I recommend grabbing my Free Beginner’s Guide to Points and Miles. It walks you through everything you need to know to start earning and redeeming points today.
1. A Family Trip to Disney World
Disney trips are magical — and expensive. Park tickets, food, and hotels can add up fast. But points can cover a big chunk of the cost.
✨ How to book it with points:
Use Chase Ultimate Rewards® or Capital One Miles® to cover Disney hotel stays when you book through their travel portals.
Marriott Bonvoy points are another great option, since there are several Marriott properties right near the parks.
Flights? Use airline miles like Southwest Rapid Rewards® or Delta SkyMiles® to cover the whole family’s tickets.
💰 Cash price vs. points price:
Example: A 4-night Disney hotel stay at $300/night = $1,200 cash.
Booked through Chase with 80,000 points (from one welcome bonus) = essentially free.
👉 Beginner Tip: Many credit card bonuses alone are enough to cover your Disney hotel stay. Pair that with airline miles for flights, and you’ve cut your trip cost in half (or more).
2. A Beach Vacation in Hawaii
Hawaii is one of the most popular bucket-list destinations for families and couples. Flights from the U.S. mainland can get pricey, often $600–$900 roundtrip.
✨ How to book it with points:
Use American Airlines AAdvantage® miles or United MileagePlus® miles — both often have award flights to Hawaii for as low as 22,500 miles each way.
Hyatt hotels in Hawaii can be a fantastic deal. For example, the Hyatt Regency Maui often goes for 25,000 Hyatt points per night (worth $500+ in cash).
💰 Cash price vs. points price:
Example: Roundtrip flight for two from New York to Maui = $1,200 cash.
Booked with 45,000 miles + $11.20 in taxes each = ~$22 total out of pocket.
👉 Beginner Tip: Transferable currencies like Chase Ultimate Rewards® or Amex Membership Rewards® can move into airline or hotel programs that serve Hawaii, giving you maximum flexibility.
3. A European Adventure (Flights for Almost Free)
Europe is where many people want to use their points first. Flights to Paris, Rome, or Barcelona regularly cost $800–$1,200 per person.
✨ How to book it with points:
Use Virgin Atlantic Flying Club miles to book Delta flights to Europe starting at 30,000 miles one-way.
Aeroplan (Air Canada’s program) is another fantastic option with low mileage requirements and plenty of partners.
For hotels, consider IHG or Marriott — there are tons of options in major European cities.
💰 Cash price vs. points price:
Example: Roundtrip New York → Paris = $900 cash.
With Virgin Atlantic: 60,000 miles + ~$100 in taxes roundtrip.
👉 Beginner Tip: Look for off-peak travel dates. A single credit card welcome bonus can cover a roundtrip to Europe if you plan smart.
4. Luxury Business Class to Asia
This is the dream redemption for many travel hackers: lie-flat seats, champagne, and gourmet meals at 35,000 feet — without the $5,000+ price tag.
✨ How to book it with points:
ANA Mileage Club (Japan’s airline) offers incredible deals on roundtrip flights to Asia in business class, often under 100,000 miles.
Alaska Airlines Mileage Plan partners with airlines like Cathay Pacific and Japan Airlines for world-class business class redemptions.
You can transfer Amex Membership Rewards® to ANA or Marriott Bonvoy points to Alaska.
💰 Cash price vs. points price:
Example: Roundtrip Los Angeles → Tokyo business class = $6,500 cash.
With ANA: 95,000 miles + ~$250 in taxes.
👉 Beginner Tip: This one takes a little more planning but shows just how much value points can unlock. Beginners who start earning transferable points now can save toward a “big dream trip” like this.
5. A Long Weekend in the U.S.
Not every trip has to be international. Points are perfect for spontaneous getaways or family visits.
✨ How to book it with points:
Use airline miles like Southwest, Delta, or United for domestic flights.
Hotels like Hyatt, Hilton, and Marriott all have affordable properties in major U.S. cities.
Even better: use credit card travel portals to book boutique hotels that aren’t part of major chains.
💰 Cash price vs. points price:
Example: Weekend trip Chicago → Miami for two = $600 cash.
With Southwest: 24,000 points + $22 taxes.
👉 Beginner Tip: Short-haul flights and weekend hotel stays are some of the easiest and most beginner-friendly redemptions.
Why These Trips Matter
The point isn’t just that you can save money. It’s that you can:
Take trips you never thought possible.
Free up your budget for experiences (not flights).
Travel more often without draining your savings.
When you realize one credit card bonus can cover a Disney hotel, or a couple of roundtrip tickets to Europe, it changes the way you see travel forever.
How to Get Started (Without Overwhelm)
If these examples have you excited but also thinking “where do I even begin?” — that’s where my Free Beginner’s Guide to Points and Miles comes in.
Inside, you’ll learn:
The difference between airline miles, hotel points, and transferable currencies.
How to choose the right starter credit card.
The top 4 beginner-friendly cards I recommend.
Mistakes to avoid so you don’t waste your first stash of points.
👉 Download it here and start planning your first free trip
Final Thoughts
Travel hacking isn’t about flying first class on every trip (though that’s fun, too). It’s about unlocking more travel opportunities — whether that’s Disney with your kids, a honeymoon in Hawaii, or a weekend getaway you’d normally skip because of cost.
The best part? You don’t have to be a pro. With just a little strategy, you can turn points into plane tickets, hotels, and memories that would have cost thousands of dollars.
So the next time you see a flight price that makes your jaw drop, remember — points and miles can make it a reality.
Ready to start your own points journey? Grab my Free Beginner’s Guide to Points and Miles and take the first step toward your next trip.