Travel Hacking 101: How to Fly Free in 2026 (Step-by-Step Guide)

Intro

Imagine booking a $5,000 business class ticket to Tokyo for $45 in taxes. It sounds like a scam, but it is the reality for millions of "travel hackers" who understand how to manipulate the credit card loyalty ecosystem. Travel hacking is the art of accumulating points and miles through strategic credit card spending—not flying—and redeeming them for outsized value.

In 2026, the game has changed slightly. Airlines have dynamic pricing, and award charts are disappearing. But the core principle remains: banks pay airlines for miles, and they give those miles to you to win your business. Here is how you take advantage of that system safely and responsibly.

Quick Summary: The Golden Rules

• Rule #1: Never carry a balance. Interest kills the value of rewards.
• Rule #2: Have a goal. Don't hoard points; earn them for a specific trip.
• Rule #3: Understand the "Chase 5/24" rule before you apply for anything.
• Rule #4: Transferable points (Chase/Amex/Capital One) > Airline miles.

Step 1: The Prerequisites

Before you apply for a single card, you need a credit score of roughly 700 or higher. You also need to be financially stable. If you have credit card debt, stop reading this and pay it off. Travel hacking is for those who treat credit cards like debit cards.

Step 2: The "Sign-Up Bonus" Strategy

The fastest way to earn points is not by spending $1 on a coffee; it is by hitting Sign-Up Bonuses (SUBs). A typical bonus might offer 60,000 to 100,000 points after you spend $4,000 in the first 3 months.

Example Math:
Spending $4,000 at 1x points/dollar = 4,000 points.
Spending $4,000 to hit a SUB = 60,000 + 4,000 = 64,000 points.
The bonus accelerates your earning by 15x.

Step 3: Transfer Partners vs. Travel Portals

This is where beginners get stuck. You have 60,000 Chase points. You could book a flight through the Chase Travel Portal (like Expedia) where points are worth fixed cash (e.g., 1.25 cents). Don't do this often.

Instead, transfer those points to a partner like Hyatt or United. 60,000 points in the portal might buy you a $750 flight. Transferred to Hyatt, those same 60,000 points could book you 2-3 nights at a luxury Park Hyatt resort worth $2,000+. This is called "asymmetric value."

Step 4: Managing the "5/24" Clock

Chase is the strictest issuer. They will not approve you if you have opened 5+ cards from any bank in the last 24 months. Therefore, your strategy in 2026 should almost always be to get Chase cards first (Sapphire, Freedom, Ink) before moving to American Express or Capital One.

Comparison: Earning Potential

Mini FAQ

Is travel hacking legal?

Yes. Banks encourage it because they make money on transaction fees every time you swipe the card. As long as you don't manufacture spending (buying money orders, etc.), you are a welcomed customer.

Do points expire?

With most major transferable currencies (Chase, Amex, Capital One), points do not expire as long as the account is open. However, once you transfer them to an airline (e.g., British Airways), they are subject to that airline's expiration policies.

What if I can't meet the minimum spend?

Time your applications around big expenses: taxes, insurance premiums, tuition, or group vacations where friends can pay you back.

Conclusion

Travel hacking is a marathon, not a sprint. Start with one good card, hit the bonus, and take a free weekend trip. Once you feel the rush of a $0 hotel bill, you will never go back to paying cash.

Action Step: Check your 5/24 status and research the Chase Sapphire Preferred.