The Extra Mile, Oct 9: Southwest’s Latest Big Move, An Awesome 10.5K Point Promo & More

🤯 Could Southwest Really Start Flying Boeing 787s Long-Haul?!

For better or worse, Southwest isn’t the beloved airline of founder Herb Kelleher anymore.

Bags fly free? Gone. First-come, first-served boarding and lining up at those goofy metal stanchions? Gone, too. New extra legroom seats and pesky basic economy fares? Here to stay, both fortunately and very unfortunately.

But this could arguably be its biggest pivot yet: The airline reportedly wants Boeing 787 Dreamliners to fly long-haul international flights.

That comes from Reuters, citing three anonymous sources “familiar with the carrier’s fleet planning.” The outlet reports no final decision has been made, and Southwest pointedly said they have no news to announce.

Still, the fact that an airline that has flown Boeing 737s and only Boeing 737s for (OK, aviation nerds know there was a brief spell flying ancient Boeing 727s in the late 70s) is even considering going down this path is just another reminder of how much the Southwest you know and (quite possibly) loved has changed within just the last few years.

It’s a sign of the times for Southwest … and the airline industry as a whole.

Long-haul flying is where the money is – and not just in the form of fares from passengers, but especially for that all-important credit card revenue. That’s where airlines make their real money these days.

To convince customers to open a credit card and spend on it, Southwest needs to convince those same flyers that its credit cards are worthwhile and that their miles are worth earning.

That’s why Southwest is doing what was once unthinkable and opening airport lounges. But as the wealthy Americans airlines are courting increasingly look overseas for their travels, Southwest needs to find a way to get them there.

Otherwise, why open a credit card and earn miles on an airline that can only get you from Nashville (BNA) to Pittsburgh (PIT) – not Paris-Charles de Gaulle (CDG)?

It won’t happen overnight – not even close. Buying a brand-new Boeing 787 isn’t like driving a new car off the lot … though Southwest could perhaps grab one secondhand from a struggling airline like Norse Atlantic.

But I wouldn’t be shocked if we hear something concrete next week at the airline’s big event down in Dallas…

– Kyle Potter, executive editor

🤝 Deal of the Day: Earn up to 10.5K Southwest Points FREE!

Heat scale (out of 3): 🔥🔥🔥

Why we love it: Because who doesn’t love free points just for uploading some screenshots?!

Southwest’s goofy “Notification Vacation” promo will give you 1 Southwest Rapid Rewards point for each unread notification on your home screen. It’s a minimum of 500 and a max of 10,000 points – plus, another 500 for a short quiz afterward.

The next round starts at 12 p.m. ET today – set your alarm!

Get ready to enter!

– Kyle Potter, executive editor

📡 On Our Radar: St. Louis to the World

Welcome to On Our Radar – a weekly look at the news and trends we’re watching lately!

⚜️ St. Louis Gets Another European Nonstop Flight

Recently, we wrote about British Airways making its nonstop route from London (LHR) to St. Louis (STL) daily in early summer – a surprising move to the Midwestern city that hasn’t had a ton of long-haul service in recent years.

And then, this week, Icelandair jumped into STL – announcing a four-times-a-week nonstop flight to Reykjavik (KEF) that is already on sale for less than $600 roundtrip all summer long and for just $495 roundtrip next August! (Pictured below as $458, but the price to book direct with Icelandair is $495.)

I’m so excited about this addition for the travelers of Greater St. Louis. Having Icelandair in town helps keep European fares cheap – not to mention connecting you directly to one of my favorite destinations on earth.

Icelandair’s KEF flight will be the airport’s third transatlantic route, joining Lufthansa’s nonstop flight to Frankfurt (FRA) and the aforementioned B.A. London flight. (Fun fact: Iberia flew to St. Louis for one year in 2013.) 2026 is already going to be the airport’s largest-ever year of transatlantic capacity, and 2027 will blow it out of the water.

Buckle up, St. Louis: Cheap flights to Europe are coming!

💰 The Race for Flagstaff, Arizona, is On

Since 2025, American Airlines has been your only choice to fly to Flagstaff, Arizona (FLG) – the closest commercial airport to the Grand Canyon (about 1.5 hours away).

Last week, Delta sought to change that by scheduling a daily nonstop flight to FLG from its Salt Lake City (SLC) hub, starting June 7, 2027. Well, United decided it wanted in on the Grand Canyon party, too – immediately retaliating with a Denver (DEN) flight that starts Aug. 10.

I love to see this. All three major U.S. airlines are fighting over a small airport, which should hopefully drive down airfare to this gateway to Sedona and the Grand Canyon.

This route is making me feel rather “booksy.” I’ve got the itch to fly to FLG this year!

– Gunnar Olson, travel reporter and flight deal analyst

👫 How & When to Book Award Flights for Others

What good are points and miles if you can’t travel with the people you love?

Here’s the problem: Booking award flights for other people isn’t always as straightforward as booking with cash. Sometimes (like on the U.S. airlines) you can just book a flight for your friends and family using miles, no problem. Other times, there are strict rules about who you can book for, how long your account is open, and where the points came from in the first place.

I’ll walk you through the things you should consider and the hoops you have to jump through to book award flights for friends and family.

❌ Don’t: Pay to Transfer Miles to Other People. Airlines will often charge you to transfer miles between accounts, and it’s almost never a good deal. For example, to transfer 30,000 Delta SkyMiles between accounts, it’ll cost you a $330 fee!

✅ Do: Book the Flight For Them Instead. You know what’s totally free on airlines like Delta? Just booking them the flight they want instead! Easy. Simple. Free.

↔️ When Does it Make Sense to Transfer Between Accounts? When it’s free!

If you have Capital One miles, you can freely combine miles between users and then transfer those points to your bank of choice. You can do the same with Chase, but only if you live in the same household (although you can get around that by sharing a last name with someone, in our experience).

With American Express, you can transfer your points to another person’s loyalty account for free … but only if they’re an authorized user on your card. And with the Alaska Atmos Rewards Summit card, you can combine Atmos between accounts for free, too.

⚠️ Airline Programs With Tricky Booking for Others Policies

Here are the airlines to watch out for:

• 🇶🇦 Qatar Airways – You must register family and friends as companions, and you have to have an account that is at least 30 days old.
• 🇯🇵 Japan Airlines (JAL) – You have to be related “within two degrees of separation” to the person you’re booking for, and your account has to be open for seven days.
• ⛩️ ANA – Similar to JAL, you have to be related to the person, and you have to register family members (up to 10 of them) to book for them.
• 🇭🇰 Cathay Pacific – You have to add people to a “redemption group” to book for them (up to five people), and it costs $50 if you want to change one of those five.
• 🇹🇼 EVA – This is the trickiest one: Every passenger must have their own EVA miles to book for them, and you have to set up a transfer nominee, which takes 24 hours.
• 🇹🇷 Turkish – If it’s your first time booking through Turkish, you have to call the airline in order to search and book for more than one passenger.
• 🇸🇬 Singapore – You can add up to five “nominees” to book for others, and you can’t change those nominees for six months, at which time they’ll cost $30 to replace.

Some of these policies are complicated, but we broke them all down in the post on our website.

– Gunnar Olson (flight deal analyst & travel reporter)

🎙️ A New Tool to Save on Flights & Other Travel News

📰 This week, the guys break down all the travel news that’s fit to podcast … and there’s a lot of it. That includes a brand-new (and free) tool to save on flights when fares drop, new big card bonus offers, 11 (!) transfer bonuses, and a deep dive on what the heck has happened with World of Hyatt.

Watch it now on YouTube, Apple Podcasts, Spotify, or wherever you get your podcasts.

🙅‍♂️ Skip This Amex Fine Hotels + Resorts® Stay in Taipei

Regent Taipei is among the most affordable Fine Hotels + Resorts® (FHR) properties in Taiwan, but it’s dated and in need of a serious refresh. On the plus side, the rooms are huge and the breakfast buffet (included with FHR bookings) was expansive.

Overall Rating: ⭐️⭐️⭐️½

Rooms: ⭐️⭐️⭐️

Grounds & Amenities: ⭐️⭐️⭐️

Service & Food: ⭐️⭐️⭐️⭐️

I’ve stayed in far, far worse hotels than the Regent Taipei. But when I book through American Express Fine Hotels + Resorts®, I expect a certain level of polish, and this one just didn’t deliver.

Call it the definition of a first-world problem.

My biggest gripe is that the Regent Taipei is woefully dated with tired furnishings, worn carpet, and decor that feels straight out of the ’90s (maybe even the ’80s?). If that’s still your idea of a five-star luxury hotel in 2026, you might walk away feeling differently.

If you’ve been following along, you know by now that a typhoon chased my wife and me out of Tokyo a day early. As a result, we needed an extra last-minute hotel night in Taipei and used an IHG anniversary night at the Kimpton Da An, which we much preferred to the Regent.

How I booked it: The main draw for this property was that the Regent is eligible for the semi-annual hotel credit of up to $300 that comes with my American Express Platinum Card®.

I booked a two-night stay for $488. After the credit kicked in, I was only out of pocket $188, or less than $100 a night for a centrally located hotel in Taipei. Hard to complain about that.

The room: In my opinion, this is where the Regent missed the mark most. The couch and armchairs look like they’re from decades gone by, and the dark wood finishes and worn carpet don’t help.

But to be fair, the room was huge, with plenty of space to spread out suitcases and hang clothes. After a cramped room in Tokyo just a few days earlier, that was a welcome change.

The bathroom was equally dated with lots of marble, but again, it was huge and included a soaking tub, separate shower, and private space (but no door) for the toilet.

Dining & Service: We only ate on-property for breakfast, but the restaurant runs an equally expansive dinner buffet at night, with prime rib, crab legs, and plenty of Asian dishes.

Service was attentive throughout, from a warm welcome at check-in to the rooftop pool and the restaurant.

Amex FHR Benefits: Beyond the $300 credit, FHR bookings come with perks like early check-in, late checkout, daily breakfast for two, an on-property credit, and a shot at a room upgrade.

Breakfast was the standout. It’s a massive buffet with both Asian and Western options, and I made a beeline for the made-to-order Taiwanese noodle station every morning.

The property credit was $150 toward the spa. Personally, I’d have preferred a food and beverage credit. Still, my wife booked a 90-minute massage (realistically about 60 minutes of massage plus 30 minutes of spa time) for just ~$25 out of pocket.

Is that a great value? Not exactly. Taipei is full of massage spots offering full-body massages for $40 or less. But the Regent’s spa is far nicer than anything you’ll find at that price point.

Early check-in came through, too. We got into our room shortly after noon, while the guest next to me at the front desk was told to wait a couple more hours.

Location: The Regent sits in Taipei’s Zhongshan District, just one stop from Taipei Main Station on the metro’s Red Line. Getting around on foot and by public transit was easy, and the handful of Ubers we took were all quite affordable.

The hotel is also part of a building that’s really more of a mall, with several luxury retailers on-site. If you’re in a shopping mood, you’ll be right at home.

Bottom line: The Regent Taipei wasn’t a bad stay. Breakfast was solid, service was attentive, the room was spacious, the location is convenient, and the Amex Platinum credit brought my cost down to $188 for two nights.

But for an FHR property, it’s showing its age, and there’s no hiding it. In hindsight, there are other similarly priced FHR hotels in Taipei that look like a much better use of that $300 credit.

– Jackson Newman, senior editor

✈️ Other Travel Tidbits

• 🎟️ A targeted Chase Offer is giving 8% back as a statement credit, up to $10 total, on Viator and TripAdvisor Experiences bookings through Oct. 31. (Frequent Miler)
• 🎁 Chase has rolled out limited-time bonuses of up to 90,000 miles on its United credit cards, or 100,000 with an authorized user added in the first three months.
• 💼 American’s free AAdvantage Business program is offering 15,000 bonus miles to new members who register with code GET15K through Oct. 31, with no activity required to earn them. (One Mile at a Time)
• 📉 Alaska Airlines has reportedly stopped repricing tickets when fares drop, instead telling customers to cancel and rebook to capture the savings, which can cause problems for Companion Fare bookings and paid seats. (View from the Wing)