Tag: Repositioning Flights

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