Category: Other Guides

How Repositioning Flights Can Unlock More Award Travel
By Manny Estrada | Published on July 23rd, 2025

You’ve run the search. You picked your home airport, adjusted the filters, checked a few dates, and the results are disappointing. Maybe nothing matches your travel window. Maybe the flights that do show up cost way more points than expected. You refresh, tweak the inputs, try again… and still come up short.

At this point, most travelers assume they’re out of luck. They either settle for something mediocre or give up entirely.

But experienced points travelers know there is another move to make. It doesn’t require changing your destination, switching programs, or altering your travel dates. It starts with one question:

What if the problem isn’t the destination… but where you’re starting from?

This is where repositioning flights come into play. By flying from a different departure city, often just a short domestic hop away, you can unlock far more award space, better itineraries, and lower points pricing. With PointsYeah, spotting these opportunities is easier than ever.

Why Your Home Airport Isn’t Always the Best Starting Point

Award availability is affected by dozens of factors, including partner networks, route demand, time of year, and airline-specific patterns. Even at major hubs like Los Angeles, Dallas–Fort Worth, Chicago, or New york, the flight you want might not show up in your search or it may cost significantly more points.

Meanwhile, another major city like Seattle or Washington D.C. might offer the exact same flight, on the same airline, at a far better redemption rate.

This is what makes repositioning so powerful. Instead of waiting for the perfect award to appear from your home airport, you take a proactive step to fly out of a city with better availability. It only takes a bit of flexibility and the right search tools.

How to Find These Opportunities with PointsYeah

PointsYeah makes this strategy easy with a tool called Daydream Explorer.

Instead of running one airport at a time, you can search by entire departure regions like United States West, United States Northeast, or United States Midwest, all in a single click. It is the fastest way to scan dozens of departure points without opening dozens of tabs or repeating the same search over and over.

Let’s say you’re based in Los Angeles. You run a standard search from LAX and find limited options. But when you search using the United States West region, you suddenly see better availability from cities like San Francisco or Seattle. You add a quick positioning flight, and now the award trip becomes possible.

This approach works across all types of travel. Whether you are flying internationally, booking domestic redemptions, or trying to match a partner program’s sweet spot, starting in the right region can make all the difference.

Washington D.C. to Madrid, Repositioning to New York

Let’s say you’re based in the Washington D.C. area and planning a Thanksgiving trip to Europe. You’re hoping to find a lie-flat business class seat using points, but every flight from D.C. is pricing well above 60,000 points each way. Nothing lines up with your dates, and none of the results feel like a good deal.

So you open Daydream Explorer and switch your departure region to United States Northeast.

That’s when it appears:

New York (JFK) to Madrid (MAD) – 43,000 points + $33

This matches your ideal departure window, and the price is better than anything you saw from D.C.

All it takes to make this trip happen is a short repositioning flight from DCA to JFK. That flight costs just $65 one-way, as shown in Google Flights, and gets you to New York in under 90 minutes.

By adjusting your starting region and adding a quick hop, you’ve gone from overpriced or unavailable options to a perfectly timed, lie-flat seat to Europe, right in time for the holidays.

San Francisco to Tokyo, Repositioning to Seattle

A traveler in San Francisco is planning a trip to Japan in early August. They want to fly in comfort, ideally in business class, but searches from SFO are either too expensive or unavailable on the dates they need.

So they open Daydream Explorer, switch the departure region to United States West, and the picture changes completely.

There it is:

Seattle (SEA) to Tokyo Narita (NRT) – 60,000 points + $18

Not only does the pricing beat anything found from San Francisco, but it’s on Japan Airlines, known for its exceptional business class experience, with lie-flat seating, elegant service, and a refined in-flight meal program.

To catch the flight, all they need is a quick positioning hop from San Francisco to Seattle. That flight costs just $69, takes just over two hours, and runs frequently.

With one small change to their departure city, they’ve gone from stuck to soaring, landing a high-end seat to Tokyo at a fraction of the points.

How to Use This Strategy the Smart Way
- Use Daydream Explorer’s region filters
  Don’t waste time guessing which airport might have better pricing. Use the regional filters to scan a wide range of departure cities at once. You can search any of the following:
  - United States West
  - United States Northeast
  - United States Midwest
  - United States Southeast
  - United States South
- Set alerts for multiple cities
  You can set up to four free alerts with PointsYeah, and even more if you’re a Premium member. These will notify you when award prices drop or new seats open up, even if it’s not from your home airport.
- Keep positioning simple
  Focus on nonstop or single-hop routes when booking your domestic flight. Use cash or miles, and leave enough time between flights to protect yourself from delays.
- Be flexible on direction
  Sometimes it makes sense to reposition only on the outbound or return leg. You might fly out of Seattle and return directly to your home city, or vice versa.
The Takeaway

Repositioning flights are one of the easiest ways to stretch your points and find better availability. All it takes is a shift in strategy.

Instead of asking, “Where can I go from here?”

Ask, “Where else could I start this trip?”

With tools like Daydream Explorer and flight alerts, PointsYeah makes this kind of flexible searching faster and smarter. You don’t need to live near the perfect airport. You just need to be willing to take one extra step, and the rewards can be huge.

Start exploring more departure regions today on PointsYeah.

A better award flight could be just one airport away.
July 22, 2025
How Buying Points Helped Me Fly My Family to Europe in Business Class for Less Than $900 Each
Flying business class to Europe as a family of four? Most people think that’s a once-in-a-lifetime splurge. But with a little strategy, the right timing, and the right tools, I made it happen for a fraction of the cost.

Here’s the full story of how I saved over $10,000 on our flights and turned a dream family trip into reality.

Step 1: Catching the Points Sale of the Year

In late 2024, Hawaiian Airlines ran a 100% bonus sale on miles. When you know how to use points, deals like this are impossible to pass up. I didn’t hesitate. I bought around 320,000 Hawaiian miles for $4,064.00 because I knew I could put them to work later.

But here’s what made this special.

At the time, there was a workaround that let you transfer Hawaiian Airlines miles to Alaska Airlines Mileage Plan. This was huge. Normally, getting points into Alaska is difficult, but this Hawaiian path opened up access to some of the best award redemptions in the game.

I didn’t know exactly when I would use the miles, but I knew the opportunity was too good to miss.

Step 2: The Search for Four Business Class Seats

Fast forward to February and March 2025. I started searching for four business class tickets from the West Coast to Europe for a late spring or early summer family trip.

Finding four seats in business class on the same flight? That’s not easy. But it’s possible if you know where to look.

I spent weeks searching, checking routes, flipping through dates, and running searches across multiple airlines. I knew I needed a tool that could keep up with me and help me move fast.

That’s why I used PointsYeah’s Daydream Explorer. It’s fast, flexible, and my absolute go-to for finding award flights. You can search across programs and dates in seconds, which saves a ton of time and opens up flights most people miss.

Then I found it.

Four business class seats from Las Vegas to Frankfurt on Condor Airlines for just 70,000 Alaska miles per ticket.

Finding one seat at that rate is pretty rare. Finding four on the same flight? That’s tough, but this is exactly what Daydream Explorer is built for. It helped me spot this deal quickly before it was gone.

I stared at the screen, double-checked the dates, the cabin, the taxes. I refreshed the page. I ran the search again. I triple-checked everything just to be sure.

It was real. And I knew I had to move fast. Deals like this don’t wait around. If you hesitate, they’re gone.

So I booked them immediately.

The trip was locked in.

The Final Numbers:
- Total Miles: 280,000 Alaska miles
- Cash Paid: $196.80 in taxes and fees
Just out of curiosity, I checked the cash price for those same flights on Google Flights.

$14,080 for 4 people.

I booked them for less than $900 per person. That’s a savings of over $10,000.

That’s not a discount. That’s a major win!

Step 3: Flying in Style

When the day finally came, it all felt surreal. We weren’t crammed in economy. We weren’t worrying about sleep, legroom, or whether our kids would be miserable for ten hours. We were flying in comfort. We were flying in business class.

Boarding Condor’s A330, we settled into wide, spacious seats that fully reclined into beds. The cabin was quiet. The service was smooth. The food was surprisingly good. And when we took off, I had this moment of realizing this is why I chase points. It’s not just about saving money, it’s about creating moments that make travel easier, more enjoyable, and more memorable.

The flight was perfect. We dined, we slept, and we landed in Frankfurt feeling refreshed, rested, and genuinely excited to kick off our European adventure.

When you travel with your family, this matters. Arriving well-rested changes everything. It sets the tone for the entire trip.

And the best part? I didn’t need to spend $14,000 to make it happen.

This is the power of points. This is why I play the game.

How Daydream Explorer Made It Happen

It’s not just fast. It’s not just easy. It’s built to help you find flights most people miss. I could quickly scan wide-open date ranges, mix and match departure cities, and explore hidden opportunities that would have been buried in endless airline searches.

While others are still clicking through airline websites, I’m already booking.

If I wasn’t using Daydream Explorer, I never would have found those four seats. I never would have pulled this off.

Looking back, this whole experience changed how I think about buying points.

Buying Points Can Be a Game-Changer When It Makes Sense

This trip really opened my eyes to what buying points can unlock. It’s not something I do for every trip, but when the right opportunity shows up, it can make a huge difference.

When there’s a big sale, when you’ve done the math, and when you can actually find the seats you want, buying points can be the key to getting incredible value. It can turn flights that seem completely out of reach into something that’s possible.

I didn’t buy points just to have them sitting in my account. I bought them because I had a real plan and a real way to use them.

Buying points isn’t always the answer, but sometimes, it’s exactly what makes trips like this happen.

Important: The Points Game Is Always Changing

When I bought Hawaiian miles last year, the Hawaiian-to-Alaska transfer path was wide open. It was one of the best workarounds in the game. That path has since closed, and it’s a perfect reminder that these windows don’t stay open forever.

Award programs, transfer partners, and sweet spots are constantly shifting. What works today might be gone tomorrow. We’ve seen it happen with Virgin Atlantic’s rising fees, Emirates’ recent Amex transfer devaluation, and other changes across the points landscape.

The key takeaway?

Maximize transfer bonuses and partner sweet spots while you can, but don’t move points speculatively. Wait until you find a real, bookable flight. Programs can devalue, transfer ratios can shift, and award space can vanish overnight.

There will always be new deals, but the industry moves fast. Staying ready, staying flexible, and using the right tools is how you stay ahead.

Final Takeaway: You Can Do This Too

Buying points when the math works out can be one of the smartest moves in points travel. You don’t have to be an expert. You just need to:
- Be ready to act when a deal drops.
- Use the right tools, like Daydream Explorer, to search smarter and faster.
- Trust the process.
This is how you win with points.
June 15, 2025
Travel Freely: The Free App That Helps You Travel More and Spend Less
At PointsYeah, we’re always looking to spotlight resources that help travelers do more with less. That’s why we’re thrilled to feature Travel Freely: a free app built for everyday people who want to maximize their points, stay organized, and earn over $2,000 in free travel each year.

Whether you’re a complete beginner or someone who already has a stash of points, Travel Freely removes the guesswork, helping you make smarter decisions about which cards to get, when to use them, and how to manage it all effortlessly.

What is Travel Freely?

Travel Freely was created by Zac Hood, a former teacher and non-profit director who discovered the world of travel rewards after booking his proposal trip to Southern France entirely with points. From there, he developed a system to stay on top of card offers, deadlines, and upgrades—without spreadsheets or stress. That system became the Travel Freely app.

Now available on both web and mobile (iOS + Android), Travel Freely helps users:
- Organize all your credit cards in one place
- Track welcome bonuses, annual fees, bonus deadlines, and downgrades
- Track your 5/24 number
- Organize card strategies for individuals, couples, and even small businesses
And the best part? It’s 100% free. No upsells, no locked features—just great tools that help you travel better.

🏆 Travel Freely users average over $2,000 in free travel per year—and some go much further.

Why Travel Freely Works

What makes Travel Freely stand out is how it turns a complicated subject into something intuitive and approachable. You don’t need spreadsheets or advanced knowledge. The app does the heavy lifting so you can focus on enjoying the journey.

✅ Beginner-Friendly Onboarding

Step-by-step guidance helps you understand the landscape and start strong—even if you’ve never used a rewards card before.

🃏 CardGenie™ Personalized Recommendations

The app recommends the optimal cards for your situation, factoring in bank rules and your existing lineup.

📅 Smart Reminders for Bonuses & Fees

Get notified before annual fees hit or deadlines expire. Never miss a bonus or downgrade window again.

👥 Built for Couples & Businesses

Track credit cards for yourself, a partner, or your business—all in one place. Perfect for maximizing rewards as a team.

🔐 Security-First Design

Travel Freely doesn’t ask for sensitive logins or personal data. You simply input your card names and open dates, and the app handles the rest.

⭐⭐⭐⭐⭐
Over 2,000 4.9-star reviews on the App Store and features in outlets like Business Insider speak to how widely loved—and trusted—Travel Freely really is.

Who Is Travel Freely For?

New to rewards? Travel Freely will guide you from start to finish, helping you avoid common pitfalls while you earn your first free trips.

Already experienced? Say goodbye to spreadsheets. Use the built-in 5/24 tracker, deadline alerts, and personalized offers to stay on top of your strategy.

Couples & Families? Coordinate cards and double your earning power with shared tracking and timelines.

Why Travel Freely and PointsYeah Belong Together

Travel Freely and PointsYeah make a powerful pair for anyone serious about optimizing their travel.
- Travel Freely helps you keep track of your rewards cards and stay organized to maximize your point-earning.
- PointsYeah helps you redeem those rewards for maximum value—whether it’s a dream hotel or a last-minute flight deal.
From first steps to first class, this duo takes the complexity out of free travel and turns it into something simple and exciting.

Try Travel Freely Today

If you’re looking to simplify your travel rewards journey—or just want to earn more free travel on your regular spending—Travel Freely is a must-try.

👉 Try Travel Freely for Free

No credit card required. No ads. Just a beautifully designed platform with one mission: to help you travel more, spend less, and enjoy the process.

Written in collaboration with our friends at Travel Freely.
June 6, 2025
How to use Points and Miles within Europe
By Sarah Cash

Key Takeaways for European Flight & Hotel Redemptions
- Low-cost redemptions beat budget airlines: Some European routes cost as little as 4,000-7,500 miles plus minimal taxes
- Orphaned miles find perfect use: Stranded airline miles and hotel points are an excellent use for short European stays
- Business class flights offer exceptional value: Premium cabin flights can cost much less using points vs. paying cash
- Transfer bonuses maximize value: Strategic transfers from credit card programs can slash redemption costs
- Flexible routing creates adventures: Use search tools to discover unexpected destinations at low mileage rates
- Hotel program perks: Know specific hotel loyalty program discounts, like getting a fifth night free when you book with Marriott Bonvoy points.
Ryanair, easyJet, and other low-cost carriers abound in Europe, setting low prices for intra-European flights. While you can typically only redeem miles for flights on more full-service airlines like Turkish Airlines and Lufthansa, that may seem like a waste of points in comparison to the cash cost. However, there are many cases and reasons why using points for flights and hotel stays within Europe may actually be the wise decision.

When Points Beat Budget Airlines on European Routes

Let’s examine a flight from Bologna to Paris. This flight costs 4,000 Virgin Atlantic Flying Club miles and $21 in taxes—an extremely low cost, even compared to the cash price of $114. Because this is such a low-cost point redemption, it makes perfect sense to use points here rather than cash.

Summer Olympics in Paris

Orphaned Airline Miles

Use Air Canada Aeroplan to fly nonstop intra-Europe

This flight from Krakow to Istanbul costs 7,500 Air Canada Aeroplan miles and $44 in taxes, compared to $138 in cash. Whether you should pay cash or use points becomes less clear-cut here. Though you come out slightly ahead when you use points, the cash cost may be low enough that you prefer saving your points for higher-value redemptions. Make sure you consider the cost of cancelling or changing the flight as well, since that is typically easy to do with an award flight, but much more costly with a cash ticket.

This scenario perfectly illustrates when you might want to use “orphaned” miles—those stranded in your airline or hotel loyalty account that cannot be transferred back to credit card programs like Chase Ultimate Rewards. These orphaned points remain in your account until they expire or are used, making intra-European flights an excellent redemption opportunity since they often cost fewer points. In short, if you have orphaned miles, or plans that may change, using points for your ticket will be more cost effective. If not, spending cash may be the smarter option if you have the money.

Maximizing Business Class Value on European Routes

Within Europe, business class journeys offer good award redemptions with much more convenience and flexibility. Take this example from Milan to Paris, which costs 8,000 Virgin Atlantic Flying Club miles and $28 in taxes, compared to $413 in cash for business class one-way.

Flying business class for your journey will help ease travel stress, especially when you’re not paying much cash. Keep in mind that European business class typically won’t include wider seats, though you will receive increased baggage allowance, plus a more premium check-in and airport experience. For example, on an economy ticket, Air France lets you take one bag up to 50 lbs, and the ticket costs $111 in cash. But for the above business class ticket, you can take two bags at up to 71 lbs each, for just 8k points + $28 in taxes. If you’re on a longer trip and are carrying more luggage, this can be a great way to alleviate travel worries, and save time and cash.

Building Flexible European Adventures with Miles

Use Daydream Explorer to help you find these hidden gems

If you’re planning a European vacation, consider building your trip around cheap flight redemptions. Daydream Explorer serves as the best flight search tool when you have date and destination flexibility. Searching from Eastern to Northern Europe over the next couple months reveals opportunities like a nonstop flight from Warsaw, Poland to Riga, Latvia for just 6,000 United MileagePlus miles and $25 in taxes—compared to $150 cash. This highlights a super low-cost way to build an adventure while making your points and miles work efficiently for your travels.

Strategic Hotel Point Redemptions

Complement your flight strategy by leveraging points for European hotel stays to create an almost entirely free vacation. Transferring Citi ThankYou points to Choice Hotels at a 1:2 transfer ratio delivers exceptional value—4,000 Citi points becomes 8,000 Choice points for a free night in Paris. Even when cash rates are relatively low, using only 4,000 points for accommodations in a major European city is difficult to beat.

Transfer bonuses apply to hotel programs just like airline loyalty programs. Through August 15, 2025, Chase is offering a 50% transfer bonus to Marriott, enabling luxury stays in Belgrade, Serbia, for 37,000 points per night at a St. Regis property. While substantial, you can optimize this redemption by combining it with Marriott’s “Fifth Night Free” benefit—stay five nights for the cost of four when booking with points. This strategy stretches your point balance while potentially accessing luxury properties that might otherwise exceed your budget.

Bottom Line: European Points & Miles Strategy

When searching for flights and hotels within Europe, follow these essential strategies: always compare cash rates against points redemptions, prioritize using orphaned points from your loyalty accounts, take advantage of credit card transfer bonuses, evaluate business class rates, maintain flexibility with both destinations and travel dates, and utilize hotel program perks like getting an extra free night.

These optimization tips help you save cash for on-the-ground adventures throughout Europe. After all, it’s a lot harder to use points and miles for your crepes and concerts than for your flights and hotels!
May 1, 2025
Why This Travel Insurance Deserves a Spot in Your Wallet
We get it, you love to travel. And if you’re here, you probably book with points and miles like a pro. You might even have a credit card that technically includes travel insurance.

So why bother reading this?

Because this one is different. It’s not just fine print on a credit card. It’s the kind of protection that actually works, and pays out fast, even on award travel. From miles redeposit fees to stolen gear, this is the kind of travel insurance you’ll wish you had, until you do.

And yes, we know that from experience.

The Flight That Turned Around, and the Claim That Didn’t

In 2022, Troy, our co-founder, was flying from Istanbul to Belgrade. A points master, travel pro, and co-founder of PointsYeah, he was halfway through the flight when the plane turned around due to weather.

Troy didn’t wait. He booked a hotel inside the terminal, paid for dinner, and went to sleep, while everyone else waited in line for airline accommodations.

A few days later, he filed a claim through Allianz. He was reimbursed without drama. No phone calls. No delays. No stress.

That moment changed how he thought about travel insurance. It wasn’t about the money. It was about keeping control of the trip when everything else fell apart.

Stolen Laptops. A Missing Wallet. Covered.

And that wasn’t the only time Allianz stepped up.

In Cancun, one laptop and an iPad were stolen from Troy’s hotel room. In Madrid, his wallet (yes, the one with 20+ cards) was snatched while he was out exploring.

Both times, he filed a claim online, uploaded the documents, and was reimbursed in less than a week.

Not every plan includes baggage loss or theft coverage, but many do. You can review the details before you buy, and if it’s not the right fit, cancel within 15 days for a full refund.

Plan changed, charged miles redeposit fee?

We all know by now that U.S. airline programs no longer charge a redeposit fee to cancel mileage bookings. However, most non-U.S. programs still do. The Annual Executive Plan will reimburse up to $500 for these fees

The Kind of Coverage That Matters

Travel insurance from Allianz is built around real-life problems, the ones travelers actually face. Depending on your plan, benefits may include:
- Miles redemption redeposit fee
- Trip cancellation
- Trip interruption
- Emergency medical and dental
- Emergency transportation
- Baggage loss, damage, or delay
- Travel delay reimbursement
- 24-hour assistance line
- Concierge support
You’ll see all of these listed in your policy documents, along with covered reasons, exclusions, and limits. The point is, this isn’t fluff. It’s designed for the kind of travel we actually do.

How It Works

Travel insurance is designed to protect you from the unexpected so you can focus on the part that matters, actually enjoying your trip.

Getting started with Allianz is simple. You don’t need to sort through dozens of policies or decode complicated language. Just follow the basics:
1. Enter your trip details Include your travel dates destination
2. Explore plan options Allianz will show you coverage options tailored to your trip.
3. Choose the plan that fits Select the coverage that works for your travel style, budget, and needs.
That’s it. No guesswork. No long forms. Just straightforward protection that travels with you.

Get started now and see your options in seconds.

The Claims Process That Doesn’t Make You Want to Scream

Allianz rebuilt their entire claims system based on customer feedback. It’s now one of the most intuitive in the industry.
- You’ll get a short walkthrough when you start your claim
- A clean dashboard shows exactly where your claim stands
- You’ll get a personal document checklist
- You can file and track everything from the Allyz app
You can also choose how you want to be paid. Direct deposit and debit disbursement are the fastest, often arriving within a few business days.

If you’re already traveling and something goes sideways, the 24-hour assistance hotline is your lifeline. From lost passports to medical emergencies, the support team is ready when you need them.

Not Sure Yet? You’ve Got Flexibility

Still not sure? Allianz offers a 15-day free look period (or longer, depending on your state). That means you can buy now, review later, and cancel with a full refund, as long as your trip hasn’t started and you haven’t filed a claim.

You don’t have to commit blindly. You can see exactly what’s included and make sure the plan fits your needs.

In other words, you can plan responsibly without overthinking it.

When One Thing Goes Wrong, You’ll Be Glad You Did

We spend hours building perfect trips. We choose routes with better aircraft, hotels with better lounges, transfer partners with better value. But even the most optimized itinerary can fall apart with one delayed flight, one missed connection, one stolen bag.

That’s why travel insurance isn’t just backup. It’s part of the strategy.

It protects your time. It protects your momentum. And it makes recovery feel manageable instead of overwhelming.

Because when things go right, you’ll never think about your policy. But when something goes wrong, you’ll feel like it saved your entire trip.

Get a personalized quote and make sure your next adventure has the backup it deserves.
April 22, 2025