How I Traveled for Free Using Chase Points

I didn’t start traveling until I met my wife back in 2019. Before then, I was the kind of person who stayed put, saved money, and didn’t really prioritize vacations. But when my wife entered the picture, travel became something we both wanted to share as part of our lifestyle. Thankfully, by the time I was ready to hit the road, I had already been quietly stockpiling Chase Ultimate Rewards points since 2016.

At first, I didn’t even know exactly how I’d use them. I just knew that these points had a reputation for being flexible and valuable. Over the years, those points have unlocked trips for us that would have cost thousands of dollars out of pocket. From our very first trip to Seattle in 2019 to our most recent family vacation in 2025, I’ve learned firsthand how powerful it can be to stick with one rewards program, use your points strategically, and let them take care of most—if not all—of your travel costs.

In this post, I’ll share my journey of how I traveled for free using Chase points, the trips I’ve taken, and my best advice for anyone looking to do the same.

Why I Started Collecting Chase Points

Back in 2011, I opened my first Chase credit card that earned Ultimate Rewards points. At the time, I wasn’t a frequent traveler. I just liked the idea of earning something back on my everyday spending. I paid my balance in full every month, so rewards were essentially “free money.”

The reason I chose Chase over other programs is simple: flexibility. Chase Ultimate Rewards points can be transferred to a wide variety of travel partners, including airlines like Southwest and United, and hotel programs like Hyatt and Marriott. They can also be redeemed directly for travel through the Chase portal at a boosted value if you have the right premium card. That flexibility was important because I didn’t want to get locked into one airline or one hotel chain.

I didn’t redeem anything for years. I just kept earning points, telling myself that one day, I’d use them for travel. That “one day” came in 2019, when I met my wife.

Our First Trip: Seattle, Washington (2019)

Our very first trip together was to Seattle in 2019. One of our friends had just bought a house and was hosting a housewarming party. It felt like the perfect excuse for our first getaway as a couple.

For the flights, I redeemed about 45,000 Chase Ultimate Rewards points through Southwest’s Rapid Rewards program for two round-trip tickets. If I had paid cash, the tickets would have cost us around $700 total.

That’s when it hit me: all those years of swiping my card and building points suddenly translated into a free trip. Instead of stressing about the cost of flights, we got to focus on enjoying the city—exploring Pike Place Market, strolling along the waterfront, and catching up with friends.

It set the tone for how I’d use Chase points moving forward: for experiences that mattered, like spending time with loved ones.

Exploring Oregon: Crater Lake, Beaverton, and Eugene (2021)

In 2021, we decided to explore more of the Pacific Northwest. Oregon had been on our list for a while, so we planned a road trip that took us through some of the state’s most iconic spots: Crater Lake National Park, Beaverton, and Eugene.

For this trip, I redeemed around 64,000 Chase points, which covered a combination of hotel stays throughout Oregon. I also used my annual free night award from my Chase credit card for one of our nights.

If we had paid cash, the trip would have cost us close to $1,000. Instead, all we had to budget for was food, gas, and activities.

Crater Lake was breathtaking—it’s one of those places that photos don’t do justice. Beaverton gave us a fun mix of city life and access to the outdoors, and Eugene was the perfect ending point with its relaxed, small-town vibe.

The fact that our lodging were essentially free made the whole trip that much more enjoyable.

Annual Anniversary Trips: Monterey and Half Moon Bay

After Oregon, my wife and I started a tradition: taking a trip every year for our wedding anniversary. These trips aren’t extravagant international getaways, but they’re meaningful and special to us.

In 2023, we spent our anniversary in Monterey, California. I redeemed about 45,000 Chase points for our hotel stay at Hyatt. The alternative would have been one thousand dollars out of pocket.

In 2024, we celebrated our anniversary in Half Moon Bay. This time, I used my annual free night award for the stay in San Carlos. Again, free accommodations meant we could treat ourselves to a nicer dinner and spend more freely on experiences.

These anniversary trips have become a tradition that I cherish. And knowing that Chase points make them affordable—or even completely free—just adds to the enjoyment.

Family Vacation with In-Laws: The Big Redemption (2025)

The biggest redemption I’ve made to date was our family vacation in May 2025. My in-laws joined us, which meant I had to cover not just travel for my wife and me, but for four people total.

I ended up redeeming about 250,000 Chase Ultimate Rewards points for:

Four Southwest tickets (round trip)
Six nights at a Hyatt hotel (two rooms)

If I had paid cash, the flights and hotel stays alone would have cost us over $4,000.

This was one of those trips where I truly appreciated all the years of sticking with Chase points. Instead of stressing about how much this family trip would set us back, I was able to use my points and focus on spending quality time with everyone. We made memories together without feeling the financial pinch.

What I’ve Learned from Using Chase Points

Looking back on these trips, there are a few key lessons I’ve learned about getting the most out of Chase points:

1. Stick to One or Two Programs

One of the biggest mistakes I see people make is spreading their points to thin across too many programs. Airlines and hotels devalue their points over time, so the more programs you’re juggling, the harder it is to build a big enough balance in any one of them to redeem for meaningful travel.

By focusing on Chase Ultimate Rewards (and transferring only when I’m ready to book), I’ve been able to consistently build enough points for redemptions that actually save me hundreds—or even thousands—of dollars.

2. Use Points for High-Value Redemptions

Not all redemptions are created equal. Using points for gift cards or merchandise usually gives you less than 1 cent per point in value. But transferring them to travel partners like Southwest or Hyatt can often get you 2–3 cents per point—or more.

That’s why I’ve always used my points for flights and hotels. The value is just unbeatable compared to other options.

3. Don’t Hoard Points Forever

Yes, points are valuable, but they also lose value over time as airlines and hotels adjust their reward charts. If you sit on them too long, you risk devaluation. I’ve found it’s best to earn with a plan in mind and redeem regularly for trips that matter.

4. Leverage Free Night Awards

Annual free night certificates from credit cards like the Chase Sapphire Preferred or Chase co-branded hotel cards can be just as valuable as points. I’ve used mine for Half Moon Bay and other stays, and those single-night redemptions often save $250–$400 each.

5. Earn Points on Everyday Spending

The best part about Chase Ultimate Rewards is how easy they are to earn. I earn them on groceries, gas, dining, and even online purchases. With bonus categories and promotions, they add up faster than you think.

Why I Recommend Chase for Travelers

If you’re new to the world of travel rewards, I recommend starting with Chase. Their points are flexible, easy to redeem, and can be incredibly valuable when transferred to the right partners. Plus, Chase cards often come with great sign-up bonuses that can give you enough points for a flight or hotel stay right out of the gate.

But the key is to stay disciplined:

Pay your balance in full every month.
Stick to one or two core programs.
Redeem for high-value travel experiences.

Do that consistently, and you’ll be surprised how quickly free trips start piling up.

Final Thoughts

Traveling wasn’t always a priority for me. In fact, before 2019, I barely traveled at all. But thanks to Chase Ultimate Rewards points, I’ve been able to say “yes” to trips that created unforgettable memories with my wife, my friends, and my in-laws—without draining our savings account.

From a $700 flight to Seattle to a $4,000 family vacation in 2025, Chase points have covered it all. And while it takes patience and planning to build up a meaningful balance, the payoff is worth it.

If you’re thinking about getting into the world of travel rewards, my advice is simple: start now, stick with one program like Chase Ultimate Rewards, and use your points for the experiences that matter most to you.

Because at the end of the day, it’s not about hoarding points—it’s about the memories those points can create.