Flights from New York to Madrid for $300 round trip, with a checked bag included? Deals like this have become rare, but Thrifty Traveler Premium’s cash and points alerts can help you find them. Premium costs about $130 a year, and one or two good deals could cover it if you’re flexible about where you go.

Meanwhile, Amex dropped big news for its Centurion Lounge network. Newark’s lounge opening has been pushed to 2027, but the delay comes with an upgrade. It’ll now be more than 30,000 square feet, making it the largest Centurion Lounge yet, complete with a gelato terrace that might even make flying out of Newark worth it. London Heathrow is also getting a second location, and Houston’s lounge is nearly tripling in size. Before any of that opens, though, Philadelphia’s lounge closes this week for renovations and isn’t expected to reopen until the end of 2027.

Even more surprising, Southwest could be eyeing Dreamliners, wide-body jets built for long-haul routes. It’d be another big shift for an airline that only recently added assigned seats and stopped letting bags fly free. We’ll believe a Southwest flight to Rome when we’re boarding it. And if you’d rather spend New Year’s Eve in flip-flops than snow boots, Andrea Bocelli and Ludacris are both headlining in the Bahamas.

👉 Get $20 off your first year of Thrifty Traveler Premium with code DEPARTUREDIGEST

Good flight deals don’t last long, so let Thrifty Traveler Premium do the hunting for you. Choose your home airport and get email alerts for everything from cheap weekend getaways to business-class seats you can book with points. Recent deals have included flights to Europe for $300 and Emirates business-class award flights to Milan.

Every deal is researched by a real team of flight experts and comes with step-by-step booking instructions. Plus, Departure Digest listeners get $20 off their first year with code DEPARTUREDIGEST.

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I just booked a flight from New York to Madrid for 300 bucks round trip. Checked bag included.

Happy Monday, and welcome back to Departure Digest. Today’s mostly about how I find fares like that, because this one probably won’t stick around long.

So, about that Madrid fare. This is on a normal airline, so I’m not getting nickel-and-dimed for every little thing. These tickets usually run at least double, and I haven’t seen fares to Europe this low in a while.

The routing isn’t perfect. I’m connecting through Colombia, which isn’t exactly on the way to Spain. That’s often the trade-off with fares this cheap. But it’s a long layover in one direction, so I’m looking at it as an excuse to get out and explore another city.

If you wanna join me, last I checked, there were still fares like this available for early February.

So here’s one of my secrets for finding cheap fares like this. It’s called Thrifty Traveler Premium.

It finds cheap flights for both cash and points. You pick your home airports, and when they spot a good fare, they email you the deal and how to book it.

There’s a free plan, but the deals show up 24 hours later, and a deal this good can be gone by then.

With the Premium plan, you also get alerts for booking with points. It’s great at finding cheap business class awards to Europe or Japan, plus some of the harder-to-book ones like Emirates first class.

Premium is about $130 a year. Premium Plus is about $190 and adds hotel deals you can book with points. One or two good deals a year, and it can pay for itself. If you wanna try it, our friends at Thrifty Traveler are giving Departure Digest listeners $20 off their first year with the code DEPARTUREDIGEST, all one word. The link’s also below.

Now, who is this actually for? If your dates are locked for a wedding or a work trip, an alert won’t magically make that flight cheap. It works best when you’re flexible enough to let the deal pick the trip. Maybe you were thinking Italy, and suddenly it’s Spain.

Thrifty Traveler also has a free credit card benefits tracker. Credit cards have low-key turned into coupon books, so I’ll take any reminder to use those perks before they expire.

And if one of those cards gets you into Amex lounges, this next one’s for you.

Last week, Amex announced what it’s calling its biggest Centurion Lounge expansion yet.

The biggest news is Newark. That lounge was supposed to open this year. Now it’s pushed to 2027, but it got way bigger, more than 30,000 square feet. That’ll make it the largest Centurion Lounge anywhere, with a bar inspired by Jersey diners and a gelato terrace.

Look, as a New Yorker, I’d normally do anything to avoid Newark. But a gelato terrace could change that.

London Heathrow is also getting a second Centurion Lounge, and Houston’s will nearly triple in size, both by 2028.

The one that matters right now is Philadelphia. That lounge closes for renovations this week. It’s not supposed to reopen until the end of 2027.

Amex lounges have been crowded for a while now. Amex first tried fixing that by changing its guesting rules, so it’s good to see them adding space this time.

Okay, from bigger lounges to bigger planes. Southwest is reportedly eyeing Dreamliners, which are big widebody planes, so it can start flying much longer international routes. Nothing’s decided yet. And new Dreamliners are basically sold out for years, so this isn’t happening anytime soon.

If it does happen, it’d be a dozen destinations at most. The goal is to keep you from switching airlines for that one big trip abroad. Between that, assigned seats, bag fees, and the lounges we covered last month, you’d barely recognize the old Southwest.

I’ll believe a Southwest flight to Rome when I’m boarding it. For now, I wouldn’t hoard Southwest points for a flight to Europe that doesn’t exist just yet.

And if you still don’t have New Year’s Eve plans and you’d rather swap the snow for sand, the Bahamas has a fun lineup.

On Dec. 31, Andrea Bocelli is performing at Atlantis. Over at Baha Mar, Ludacris headlines that same night. Then on Jan. 2, Alex Warren plays a beach concert back at Atlantis.

Honestly, I usually prefer a more low-key New Year’s Eve, but if I’m going big, I’d at least want it to be somewhere warm.

Bocelli or Ludacris at midnight is a very specific personality test.

Okay, let’s do a quick recap. If you’re flexible, let the deals come to you. If you’re an Amex lounge regular, you’ve got some bigger, better spaces to look forward to. And Southwest to Europe is still a long way off.

Pick your countdown, and I’ll talk to you soon.