Free Travel with Credit Cards

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Here’s how to get free travel with credit cards. I’ll share my strategies for maximizing points on the best credit cards for travel perks and rewards.


“teachingmillionaires.com has partnered with CardRatings for our coverage of credit card products. teachingmillionaires.com and CardRatings may receive a commission from card issuers. Opinions, reviews, analyses & recommendations are the author’s alone, and have not been reviewed, endorsed or approved by any of these entities.”


My family loves to explore new places on vacation. One of the best things we’ve done to help us afford travel is to maximize offers from credit card companies.

Recently, I was able to use credit card points and miles to go on a free vacation with my family of four.  Our free travel included flying to Florida and staying in the beautiful Hyatt Regency Clearwater Beach Resort and Spa.

Free Travel with Credit Cards


How do you get free travel with a credit card?

Let’s talk about airfare tickets first. Flying with a family of four is expensive. The secret weapon we’ve used for the past few years is the Southwest Companion Pass.

How does the Southwest Companion Pass Work? 

The Companion Pass allows you to purchase a ticket with cash or Southwest Rapid Rewards points and then book a second “companion” ticket for free.  You only pay a small amount to cover the taxes and fees for the companion ticket.

How do you get the Southwest Companion Pass?

We got our Companion Pass by accumulating 125,000 Southwest Rapid Rewards points in a calendar year and by strategically using two Southwest Airlines Chase credit cards. Another way you can earn the Southwest Companion Pass is by flying 100 qualifying one-way flights. One great thing about this travel perk is that once you earn it, you can use it for the remainder of the year in which you earned it as well as the following calendar year.

I did a podcast episode on the Southwest Companion Pass that you can listen to here

Get $25 when you sign up for a free money account and deposit $10!

Our trick to earning enough points for the Southwest Companion Pass is to get two Southwest Airlines co-branded Chase credit cards: a personal card and a business card. Depending on the signup offers at the time you apply, it’s possible to earn 125,000 points with your normal spending plus your signup bonuses.

Timing is critical for maximizing your Companion Pass. Because you can use it for the remainder of the year in which you earn it, plus the following year, you’ll want to have all of the points necessary as early in the calendar year as possible.

For example, let’s say you apply for the two Southwest credit cards later in the calendar year, and you hit the signup bonuses in December.  Well, that’s not good because then all of those points are attached to December.  When January hits, the calendar starts over and so does your Companion Pass progress.

This is NOT what you want to have happen! 

The better choice to maximize the Southwest Companion Pass is to apply for each credit card over the course of a few months, and then hit the minimum spending requirements to get the bonuses in January or February.

As a result, you’ll have nearly two years of Companion Pass use as well as a ton of Southwest points available to book your flights. Being able to book a free companion ticket every time you fly (minus minimal taxes and fees) is a game changer for travel and one of the most coveted travel rewards out there. 

free travel with credit cards

How can I get a free flight?

My wife has the Southwest Companion Pass right now.  On our recent trip, we were able to book her ticket using Rapid Rewards points and then book my companion ticket for free. We also booked a third ticket using points for our son, and our other son flew for free as a lap child.

All in all, we purchased two tickets using Rapid Rewards points, but all four of us were able to fly together because of the Southwest Companion Pass.

What credit card gives you the best travel rewards?

For our Florida trip, we utilized rewards from two credit cards: the World of Hyatt Credit Card and the Chase Sapphire Preferred Credit Card. Both of these cards offer excellent travel rewards, and I’ll share with you how to best maximize them.

A few years ago, I opened the World Of Hyatt Credit Card. The signup bonus was 30,000 points if we met the minimum spending requirement of $3,000 in three months. We also earned an additional 30,000 points by spending $15,000 over the course of six months.

Simply put, we spent an average of $2,500 per month in order to reach both bonus thresholds.  We put most of our routine expenses on this card including daycare, groceries, and gas. That enabled us to reach the threshold and earn the bonus points.

One of the main reasons I wanted to stay at the Hyatt Regency Clearwater Beach Resort and Spa  is that they have two-bedroom, two bath suites.  These rooms can go for around $1,000 per night. It isn’t always easy to stay away from home longer than a week when you are traveling with kids, so we decided to stay for six nights.

We had 60,000 Hyatt points available from our World of Hyatt Credit Card, which was enough for a little more than two nights in a standard room going for 25,000 Hyatt points per night.  However, we still needed to find points to cover the other four nights. That’s where the Chase Sapphire Preferred comes into play.

Because I already had a Sapphire card, my wife signed up for one to earn the points we needed for this trip.  The Chase Sapphire Preferred had a 60,000 bonus point offer after you spent $4,000 in the first three months.  These offers can change frequently, and I’ve seen them as high as 100,000 bonus points.

One truly unique feature of the Sapphire line of credit cards is that they have travel partners. This means that those 60,000 points can be transferred to other hotel chains, and one of them happens to be Hyatt.

Therefore, the signup bonus for the Chase Sapphire Preferred–combined with the points we earned on the money we spent to reach the bonus threshold–gave us enough points for the remaining four hotel nights.

You Also Might Like: How Can I Get Discounts on Cruises?

Are travel rewards credit cards worth it?

Yes!  We were able to book four round-trip tickets to Florida and six nights at a four-star hotel using points from travel rewards credit cards. Are travel rewards credit cards worth it? YES!

What credit cards give you free travel insurance?

Besides free hotel rooms, I wanted to share some other travel benefits that you can receive when using your Chase Sapphire Preferred.

  • Trip Cancellation and Interruption Insurance: If you use an eligible Chase card or rewards to purchase a “pre-paid tour, trip, or vacation” you are covered for up to $5,000 per trip and $10,000 per occurrence if a covered loss prevents you from traveling on or before the departure date, causes you to cancel, OR if a covered loss interrupts your covered trip.
  • Auto Rental Collision Damage Waiver: If you use an eligible Chase card to initiate and complete the entire rental transaction AND decline the company’s collision damage waiver or loss damage waiver, you will be reimbursed for collision damage or theft for most rental vehicles in the U.S. and abroad.

Using the free travel insurance provided by the Chase card is a great way to save money on your vacation.

Related Content: How Do You Get Targeted Offers from Chase?

Apply For Your Small Business AMEX Credit Card

The $20 Trick

One trick that has absolutely nothing to do with credit cards is something anyone can try in order to get an amazing hotel room upgrade. Depending on what you are going for, this is sometimes called the $20 Trick, the $50 Trick, or the $100 Trick.

The room we were able to book using our Hyatt points was beautiful, but what I was aiming for was an upgrade to the two-bedroom, two bath suite. Using this trick we got our room upgraded, and the hotel threw in free breakfast during our entire stay!

Here’s how it works:

When you check in at the hotel, they always ask you for a credit card and your ID. Slide either a $20, $50, or $100 bill in between the two cards. They’re going to separate the two cards and put them down on the counter.

Depending on the employee, he/she/they will either: 

  1. Put the money back in front of you as if you didn’t mean to give it to them OR
  2. Ask you if you need any change

And all you do is you look at them and say, “No, that’s for you.”

Then add in, “I did want to ask if you have any suite upgrades available?”

Not only did you probably just make someone’s day with a nice tip, but now if they have an upgrade available they are going to most likely give it to you.

We’ve done the $50 Trick successfully in Las Vegas, and the $100 Trick worked for us in Florida as well. 

Let’s just say this trick only works 50% of the time.  Keep in mind, the rooms we were going after for this trip were $1,000 per night not including taxes, fees, and resort fees. For us, the $100 Trick worked, and it got us well over $7,000 in value!

Not only did we get a suite upgrade, but our hotel concierge also threw in free breakfast for the entire family.

We’re not talking about a simple breakfast buffet – it was a gourmet made-to-order breakfast. And because we were in the two-room suite, they recommended we order right to our room. 

Room service was a much easier option with the kids, so we tipped the employees who brought up the food.  This minor additional cost was well worth it to us because we easily saved over $600 on meals.

If you’re tempted to try “The Trick” then start small with $20 your first time. I went BIG with the $100 Trick because I knew there were available suites, and we were staying for nearly a week. There are no guarantees, but the risk can definitely be worth the reward. 

Related Content: How to Get Free Hotel Rooms?

Key Takeaways

Free travel with credit cards is definitely possible and absolutely worth it. It takes some planning and effort as well as maximizing your everyday spend. I hope my strategies for earning travel with credit cards can help you to plan your own future getaways. 

If you are interested in more content like this, let me know down below in the comments. 

Get $25 when you sign up for a free money account and deposit $10!

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As always, I’m Rich and until next time.

“teachingmillionaires.com has partnered with CardRatings for our coverage of credit card products. teachingmillionaires.com and CardRatings may receive a commission from card issuers. Opinions, reviews, analyses & recommendations are the author’s alone, and have not been reviewed, endorsed or approved by any of these entities. Responses are not provided or commissioned by the bank advertiser. Responses have not been reviewed, approved or otherwise endorsed by the bank advertiser. It is not the bank advertiser’s responsibility to ensure all posts and/or questions are answered. I am not a financial advisor. The information I share is for educational purposes only and shouldn’t be considered as certified financial or legal advice. It is imperative you conduct your own research. I am sharing my opinion only.”

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