How To Earn Points and Miles For Free Travel

Oct 5

If you’ve just discovered the world of points and miles, you might be wondering: where do all these points actually come from? The truth is, most travelers aren’t earning millions of points by flying every week. Instead, they’re earning them through strategic credit card rewards and optimized everyday spending.

For a beginner, understanding the hierarchy of earning is key. Here is a simple breakdown of the main ways to earn points and miles—starting with the most powerful strategy of all.

Some links in this article may contain referral or affiliate links.

1. Credit Card Sign-Up Bonuses (The Single Most Powerful Strategy)

If you remember just one thing from this post, let it be this: sign-up bonuses are the fastest, most lucrative way to earn points.

When you open a new rewards card, you’ll usually be offered a large chunk of points after meeting a minimum spending requirement (a spending threshold you must reach within the first few months).

The Math Behind the Magic

Example 1: Chase Sapphire Preferred® often offers 60,000 points after you spend $4,000 in 3 months. That's worth at least $750 in travel through the Chase travel portal, or potentially much more when transferred to airline and hotel partners.
Example 2: Capital One X Venture often has a 75,000-mile bonus, worth $750 or more toward travel.

These bonuses are the difference between a few thousand miles earned over a year of spending and a round-trip international flight earned in just three months. They represent the biggest initial influx of points you will ever receive.

Consider this: The average credit card user might spend around $1,500 per month. On a standard 1x points card (meaning you earn 1 point per dollar spent), that's 18,000 points in a year. However, a single sign-up bonus—like 60,000 points after a three-month spend of $4,000—instantly provides more than triple that annual earning.

In the points world, 60,000 to 80,000 points is often enough to secure a couple round-trip economy flights to Europe, or a one-way business class ticket to Asia (especially when utilizing partner transfer sweet spots). They represent the biggest initial influx of points you will ever receive.

Critical Strategy: The Chase 5/24 Rule

Because sign-up bonuses are so valuable, the banks limit who can receive them. For beginners, the most important rule is the Chase 5/24 Rule.

If you have opened 5 or more personal credit cards from any bank in the last 24 months, Chase will automatically deny you for their rewards cards, including the highly recommended Chase Sapphire cards.
Actionable Advice for Beginners: Because Chase offers some of the most valuable and flexible transferable points, and they have many awesome travel credit cards, most experienced points collectors recommend prioritizing your first few Chase card applications before moving on to cards from other banks. While you can eventually exceed 5/24 and enjoy cards from issuers like Amex, Capital One, and Citi, securing your foundational Chase cards first ensures you don't miss out on them later. And that being said, you can still sprinkle in applications with other banks in between Chase applications, just be mindful of the 5/24 rule.

You can check out my youtube video on the 5/24 rule here.

**Chase 5/24 Rule EXPLAINED: Why You Got Denied (And How to Avoid It)**

2. Leverage a Player 2 (The Household Double-Dip)

Most rewards cards let you earn extra points by referring someone else. This is one of the most powerful strategies for families and couples, often called the "Player 2" strategy.

Referral Bonus: If you already have a card (e.g., the Chase Sapphire Preferred), you can send a referral link to your spouse, partner, or friend. If they open the card through your link, you’ll get a referral bonus (often 10,000–20,000 points).
Sign-Up Bonus: Your "Player 2" will also get their own large sign-up bonus.

This strategy effectively doubles the total points earned for the household and instantly funnels a large referral bonus into your primary points account.

How do you actually convince your partner to travel hack with you? If your partner needs a little more convincing, you should check out my video HERE where I give you actionable strategies to onboard your player 2.

How to Convince Your Player 2 to Travel Hack With You

3. Maximize Every Dollar with Strategic Spending

Once you've secured a sign-up bonus, your day-to-day use of the card becomes the next, long-term layer of strategy. This is how seasoned travelers fund their trips year after year.

The Golden Rule: Put All Expenses on Your Credit Card

This one’s simple but crucial: every expense you can, run it through your rewards credit cards.

The Accumulation: Groceries, gas, phone bills, streaming services, insurance payments—it all adds up. Even things like rent, tuition, or taxes can sometimes be paid with a card. Sometimes it even makes sense to pay a small fee in order to use a credit card, though you’ll want to weigh the transaction fees against the value of the points earned.
The Key to Responsibility: Remember the Golden Rule: always pay in full each month so interest charges don't wipe out your rewards. I like to set all of my cards on auto-pay so that the statement balance is automatically paid on the due-date. That way I never miss a payment and I never pay interest.

Optimize Earnings: The Wallet Strategy

Instead of using one card for everything, the true power of earning lies in having a small portfolio of cards that cover your biggest spending areas, minimizing the number of purchases that earn only 1× (the lowest rate).

Use Bonus Categories to Multiply Earnings

Many cards are designed to reward spending in specific categories. Using the right card for the right purchase is called "wallet optimization”.

The types of bonuses fall into two main groups:

Fixed Bonus Categories: These are reliable multipliers for common, high-spending categories. They do not change.
Examples: 3x points on all Dining and Travel (Chase Sapphire Preferred); 4x points on U.S. Supermarkets (Amex Gold); or 3x points on Gas and Groceries (Citi Strata Premier).
Rotating Bonus Categories: These cards (like the Chase Freedom Flex) offer a huge multiplier, often 5x points, but the category changes every three months.
- Examples: Quarter 1 (Q1) might be Groceries, Q2 might be Gas Stations, and Q4 might be Amazon. These typically have a spending cap (e.g., $1,500 per quarter) and must be manually activated each quarter. Missing the activation means missing the 5x bonus.

Cover Your Catch-All Spending (The Everything Card)

No matter how well you optimize, some purchases won't fit a bonus category (e.g., medical bills, random online purchases, utilities). This is why you need a card that offers better than 1x points on all other spending.

Look for a card with a flat rate of 1.5x or 2x points on all purchases (like the Chase Freedom Unlimited or Capital One Venture X). This ensures that every miscellaneous bill or unexpected expense is still earning a respectable return.

Pro Tip: Sign-Up Bonus Always Wins. While category bonuses are great for long-term earning, always prioritize meeting a new card's minimum spending requirement. A card offering 60,000 points for $4,000 in spending is an effective return of 15× points (60,000/4,000=15). Nothing else you do (not even a 5x category) comes close to that return, so put all your spending on the new card until the bonus is secured.

The Beginner’s Goal: Building a Trifecta

The ultimate goal for many points collectors is establishing a coordinated set of cards, often called a "Trifecta", from the same bank (like the Chase Ultimate Rewards family). These sets allow you to pool all your points into one powerful account (like the Sapphire card) and then transfer them out for maximum value. By strategically using 2-3 cards, you can achieve a high multiplier for almost every dollar you spend.

4. Double-Dip with Shopping Portals and Offers

These methods are low-effort ways to layer on extra points onto purchases you were already going to make, transforming a regular online purchase into a points-earning triple-dip.

Shopping Portals: The Digital Shortcut to Extra Rewards

Before you buy something online, always check if you can earn extra points or miles by starting your purchase through a shopping portal.

How it works (The Stack): You visit the portal, click the link to the retailer (like Macy's), and the portal tracks your purchase via cookies. This earns you extra rewards on top of the points you already earn by paying with your credit card.

Portal Types to Know:
- Bank Portals (e.g., Shop Through Chase, Capital One Shopping): Offer bonus points directly into your main bank currency. Sometimes it requires you to use a specific credit card as well as clicking through the portal.
- Airline/Hotel Portals (e.g., American Airlines AAdvantage eShopping, United MileagePlus Shopping, etc): Gives you bonus miles in a specific loyalty program.
- Cash Back/Hybrid Portals: Sites like Rakuten offer cash back, but also allow you to convert those earnings into valuable transferable points (American Express Membership Rewards), often at a favorable rate. Others just offer straight cash back, or points that can be redeemed for giftcard purchases.

My Favorite Shopping Portals:

Rakuten: This one is my favorite because it allows you to choose between cash back or Amex Membership Rewards points, offering immense flexibility and the potential for high-value redemption. I have personally earned well over 100,000 Amex Membership Rewards just from my normal spending.
TopCashBack: Known for often having some of the highest cash back rates available, making it essential to check and compare before a major purchase.
Capital One Shopping: Excellent for automatically finding coupon codes and comparing prices across different retailers. This one is known for emailing you targeted and often very high bonuses. The key to using this one is to browse a website in a browser that has the Capital One extension installed. Don’t make a purchase yet; wait a day or two, and often times you will be emailed an elevated cash-back bonus for shopping on that website because Capital One can see that you have shown interest in that website.

Card-Linked Offers

Many banks offer Card-Linked Offers, which are special limited-time discounts or bonus rewards tied directly to your credit card. The key is that you must manually "add" or "activate" the offer to your card before using it to shop with the specified merchant.

My favorite tool to use to manage and maximize card offers is called CardPointers. Managing these dozens of offers across multiple banks can be tedious. CardPointers is a powerful tool that helps you automatically track, activate, and manage all your bank's limited-time offers, ensuring you never miss a deal. You can get an exclusive 30% discount on their Pro membership here: www.cardpointers.com/mileswithmary

If you want a quick review of CardPointers to learn how it works, check out my video HERE:

Maximizing Credit Card Rewards with CardPointers - Full Guide

5. The (Small) Role of Flying and Hotels

Yes, you can earn points from actually flying on planes or staying in hotels—but for beginners, this isn’t the main, high-volume earning strategy.

Credit Cards vs. Actual Travel

A single domestic flight might earn you 500–2,000 miles. Compare that to a 60,000-point credit card sign-up bonus, and you’ll see why the initial focus is on cards, not flying. Your earning rate from travel purchases on a bonus category credit card is almost always higher than the base rate earned directly from the airline/hotel loyalty program.

The Real Value of Loyalty Accounts

However, maintaining loyalty accounts is absolutely necessary for two main reasons:

Redemption & Transfers: You must have an active loyalty account (e.g., United MileagePlus, World of Hyatt) before you can transfer your valuable, flexible points (Chase, Amex) to them.
Perks & Retention: Your loyalty number is key to unlocking benefits that matter:
- Status Boosts: Many co-branded credit cards (like a Marriott or Hyatt card) automatically grant you mid-tier status, which then earns you more points on top of your stay, alongside perks like free breakfast, late checkout, and room upgrades.
- Non-Expiration: Making a small purchase or earning miles/points through the program often resets the expiration clock for your entire balance.

Still, always attach your frequent flyer or hotel loyalty number when booking, since every little bit helps keep your account active and growing.

The Golden Rule of Points: Financial Responsibility

The key to a successful, sustainable points and miles strategy is simple: Always pay your balance in full every single month.

Interest charges and credit card debt will quickly wipe out any value you gain from your rewards. Points and miles are only "free" travel if you never pay interest. Protecting your credit score and maintaining financial discipline must always be your top priority. I personally recommend utilizing auto-pay. Every time I get a new credit card, the first thing that I do is set it on autopay to pay the statement balance in full on the due date. That way, I never pay any interest, and I never need to worry about having a late payment.

Key Takeaway for Beginners

The big secret of the points and miles world is this: most of your rewards will come from credit card sign-up bonuses and smart spending strategies, not from flying.

Start Strong: Prioritize one valuable card with a large welcome offer (like the Chase Sapphire Preferred, Capital One Venture, or Citi Strata Premier) and be mindful of the Chase 5/24 Rule.
Optimize: Use your cards for every expense, and learn how to use bonus categories and shopping portals.
Be Disciplined: Pay your balance in full, every month, without exception.

With just a couple of sign-up bonuses and smart use of your cards, you can easily cover a vacation each year—often worth thousands of dollars.