How to Book Flights and Hotels for Free: Real-World Examples

Booking flights and hotels with points isn’t just a dream—it’s a smart and realistic travel strategy that can save you thousands. With the right planning and points programs, you can turn everyday spending into free travel experiences.

In this article, we’ll walk through real-world booking examples that show exactly how many points you need, which programs to use, and how to make the most of your rewards.

Example 1: Round-Trip Flight from New York to Paris in Economy

Airline: Air Canada (Aeroplan)
Program Used: Aeroplan
Cost in Points: 60,000 Aeroplan points (30,000 each way)
Taxes/Fees: ~$100 USD

How to Earn the Points:

• Aeroplan credit card signup bonus: 50,000+ points
• 1–2 months of everyday spend with the card: 10,000 points

Why It Works:
Aeroplan offers fixed-value partner awards, and Europe in economy is consistently around 60,000 points round-trip. It’s one of the best values in transatlantic travel.

Example 2: Business Class to Tokyo with United Miles

Airline: ANA via United MileagePlus
Program Used: MileagePlus
Cost in Points: 70,000 miles one-way in business class
Taxes/Fees: ~$50–80 USD

How to Earn the Points:

• Chase Sapphire Preferred signup bonus: 60,000–75,000 points
• Transfer 70,000 to United

Why It Works:
United has great award availability with ANA (a Star Alliance partner). With no fuel surcharges and low taxes, this is a high-value redemption (ticket value ~$4,500).

Example 3: 5 Nights at a Hyatt Hotel in Mexico

Hotel: Hyatt Ziva Puerto Vallarta
Program Used: World of Hyatt
Cost in Points: 100,000 points (20,000/night with 5th night free)

How to Earn the Points:

• World of Hyatt Credit Card bonus: 60,000 points
• Transfer 40,000 points from Chase Ultimate Rewards

Why It Works:
Hyatt points are among the most valuable, and their award chart is still predictable. With free meals and drinks included at Hyatt Ziva, this redemption offers significant all-inclusive value.

Example 4: Marriott Stay in New York City for a Weekend

Hotel: Moxy NYC Times Square
Program Used: Marriott Bonvoy
Cost in Points: 90,000 points (30,000/night x 3 nights)

How to Earn the Points:

• Marriott Boundless credit card: 100,000-point intro bonus

Why It Works:
Dynamic pricing means weekend stays may cost less. Booking with points can save $800–$1,000 on a weekend hotel stay in Manhattan.

Example 5: Hilton Free Night at a Beach Resort

Hotel: Hilton Hawaiian Village
Program Used: Hilton Honors
Cost in Points: 70,000–80,000 points

How to Earn the Points:

• Hilton Surpass or Aspire card welcome bonus: 130,000+ points

Why It Works:
Hilton credit cards often come with free weekend night certificates, which can be used at high-cost resorts. Combining that with points or a second certificate makes a perfect 2-night free escape.

Example 6: Family Trip with JetBlue Points

Flight: Los Angeles to Cancun for a Family of 4
Program Used: JetBlue TrueBlue
Cost in Points: 60,000 points (15,000 per person round-trip)
Taxes/Fees: ~$100 total

How to Earn the Points:

• JetBlue Plus Card bonus: 60,000 points

Why It Works:
JetBlue’s points value tracks closely with cash prices. Booking with points eliminates fare increases during school holidays.

Key Tips to Replicate These Redemptions

1. Apply for a Travel Credit Card
   Many redemptions start with a welcome bonus of 50,000–100,000 points.
2. Use Transferable Points
   Chase Ultimate Rewards, Amex Membership Rewards, and Capital One Miles give you flexibility to move points where you need them.
3. Be Flexible with Dates and Destinations
   Award availability changes often. Flying mid-week or traveling off-season gives you better chances of scoring a deal.
4. Combine Points with Perks
   Look for 5th night free offers, suite upgrades, lounge access, and waived fees based on elite status or credit card perks.
5. Book Early, Watch for Sales
   Award space disappears fast. Monitor fares and book 6–10 months in advance if possible.

Final Thoughts

Booking flights and hotels for free is more than possible—it’s predictable when you know how each loyalty program works. These real-world examples show that with just one or two strategic credit card bonuses and some planning, luxury travel can be within reach for almost anyone.

Whether it’s a solo trip to Tokyo, a romantic weekend in NYC, or a family vacation to the beach, points and miles are your ticket to seeing the world for less.

Start earning today—and your next trip could be free.