The Upgraded Points Podcast

Three topics worth your time this week, and a listener question that opens up a real debate.

Chris used the free night certificate from his Marriott Bonvoy Brilliant® American Express® Card at the Ritz-Carlton Orlando Grande Lakes against an $850 cash rate, got a last-minute upgrade and 4pm checkout thanks to Platinum status, and shares why a card that is always on the chopping block just earned another year.

He also tried Gameway at JFK, the gaming lounge accessible with Priority Pass, and is already planning to bring his son next time. 🎮

Katie flew Delta Premium Select to and from Athens, shares an honest take on bulkhead versus non-bulkhead premium economy, and opens up a bigger question. Is premium economy actually enough on long-haul flights? And at what point does a complicated itinerary with extra legs just to fly business class become more trouble than it’s worth?

Plus, a listener booked a big Hawaiian vacation with points and wants some feedback…

Marriott Bonvoy Brilliant American Express Card — Full Review [2026]
https://upgradedpoints.com/credit-cards/reviews/marriott-bonvoy-brilliant-american-express-card/

The Ritz-Carlton Orlando, Grande Lakes [In-Depth Review]
https://upgradedpoints.com/travel/hotels/ritz-carlton-orlando-grande-lakes-review/

• (00:00) - The Upgraded Points Podcast Episode 81

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Creators & Guests

Katie just got back from Greece, where she checked out some of Hilton’s latest and greatest properties...

But first, we had to pause our Mexico work trip to bring you Southwest’s new announcements because we didn't want to wait until the next episode. New status tiers, Companion Pass changes, a devaluation buried in the FAQ that they did not put in the press release, and the Southwest Icon Lounge name and design details. This is a quick overview with a full dedicated episode coming before the January 1 changes go live.

Then it’s Greece. Katie joined Hilton on a press trip covering three properties across Crete and Athens. The brand new Hilton Chania Old Town has a private in-room sauna and rooftop pool. Casa Delfino is a family-owned SLH property in the heart of old town. And the Conrad Athens with Acropolis views makes for an epic redemption.

Plus, Chris shares a stay at the YOTEL Boston listener question and a sweepstakes winner update worth hearing.

✈️ Learn more at https://upgradedpoints.com/

📧 Questions? Email us at [email protected]

Southwest Revamps Rapid Rewards Status With New Platinum Tier and Milestone Rewards
https://upgradedpoints.com/news/southwest-rapid-rewards-changes-2027/

Targeted Marriott Offer for 2 Free Nights:
https://upgradedpoints.com/news/marriott-bonvoy-targeted-promotions/

Hilton Chania Old Town Resort & Spa Review:
https://upgradedpoints.com/travel/hotels/hilton-chania-old-town-resort-spa-review/

Conrad Athens The Ilisian Review:
https://upgradedpoints.com/travel/hotels/conrad-athens-the-ilisian-review/

• (00:00) - The Upgraded Points Podcast

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Creators & Guests

IHG just refreshed its entire credit card lineup, and there is a lot to unpack.

Before the main segment, Chris shares a quick New York City stay that included two surprisingly strong award redemptions, a La Quinta in Times Square for 30,000 points against a $700 cash rate, and a voco Times Square for 42,000 points at the last minute with rooftop bar access and Times Square views. Plus an Uber Shuttle tip for getting to JFK for $25.

Then it's the main event. IHG launched a brand new premium card at $350 with a 200,000 point welcome offer, overhauled three existing cards with higher annual fees and new benefits, and made one change to the no-fee card that is a significant downgrade. Chris and Katie break down every card, what changed, what stayed the same, and whether the new lineup is worth it.

• (00:00) - The Upgraded Points Podcast Episode 79

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Creators & Guests

Most people pack their carry-on the same way every trip and wonder why they always run out of space. In this episode, Chris and Katie share the hacks that actually make a difference, from why packing cubes might be hurting you in your roller bag to how coordinating colors before you pack changes everything.

They cover roller bag strategy, personal item essentials, what to always have accessible on the plane, and the exact bags they are currently traveling with after years of heavy use.

Plus, the new Chase Freedom Flex 5% categories are live for the quarter, and Katie stacks three Hilton card credits on a Conrad Las Vegas stay.

Chapters:
00:00 The Upgraded Points Podcast Episode 78
01:12 New Freedom Flex Card 5% categories
02:23 Conrad Las Vegas at Resorts World
06:46 Carry-on roller bags
07:17 Packing cubes vs. packing flat
10:56 Travel toiletry bags
12:17 Packing for a winter trip
14:47 Headphones hack
16:16 Charging cords pouch
18:18 The carry-on gear we actually use

New Chase Freedom Flex 5%-7% Bonus Categories [Q4: October to December]
https://upgradedpoints.com/news/chase-freedom-5x-categories/

Conrad Las Vegas Review:
https://upgradedpoints.com/travel/hotels/conrad-las-vegas-review/

Monos Carry-On Pro & Monos Checked-In Medium Luggage Review
https://upgradedpoints.com/travel/monos-luggage-review/

Creators & Guests

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A lot just happened in the points and miles world. Citi added JAL Mileage Bank as a transfer partner with a 30% bonus through October 24, and it changes the math on how to use ThankYou Points for Japan and Oneworld bookings.

Hyatt officially ended its American Airlines partnership and announced a new one with Delta hours later. Chase Sapphire Reserve anniversary offers are live with up to $350 back on select purchases, some expiring as soon as October 16.

Alaska's Choose How You Earn feature is rolling out ahead of a January 1, 2027, start date. And Apple dropped the iPhone Duo, a foldable phone that folds to the size of a passport, plus AirPods 5 with real-time Live Translation that could change how you travel internationally.

Plus, Katie shares whether the new AA Executive Card vacation credit was actually worth using, and a Chase 10 million points giveaway you can enter right now.

Let’s get into it!

• (00:00) - The Upgraded Points Podcast Episode 77

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Creators & Guests

With just 3 months left in the year, now is the time to audit every credit card benefit, free night certificate, and elite status threshold before December 31 resets everything. In this episode, Chris and Katie go through the full end-of-year checklist for points travelers.

Annual credits expiring December 31 across Platinum Card® from American Express, Chase Sapphire Reserve®, Hilton Honors American Express Aspire Card, Delta cards, Citi, Bilt, and Bank of America. Free night certificates tied to calendar year spend thresholds, hotel and airline elite status qualification deadlines, Southwest Companion Pass, and how to start planning now for a strong 2027.

Plus, Katie reviews the Andaz 5th Avenue in New York, Chris covers the new Gateside by TSA PreCheck, and we answer a listener's question about the best airport strategy for a family of four near EWR.

Creators & Guests

• (00:00) - The Upgraded Points Podcast Episode 76

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Southwest is making some of the biggest moves the airline has seen in years. In this episode, Chris and Katie break down everything that's been announced, starting with Southwest's first-ever airport lounges debuting in late 2027 with at least 11 locations planned. The first four are Austin, Baltimore, Honolulu, and Nashville, and Chase is involved in the development, which means a new premium Southwest credit card is coming alongside them.

They also cover Southwest's growing list of international airline partners, now at 11 total after a new interline agreement with LOT Polish Airlines launched September 1, and what that actually means for booking international itineraries.

Plus, Chris shares his third year at Halloween Horror Nights at Universal Orlando, Katie revisits the Aruba Marriott after its full room renovation, and a listener question about booking flights to Brazil for the FIFA World Cup, with Chris answering from personal experience.

Southwest Airport Lounges Are Coming in 2027:
https://upgradedpoints.com/news/southwest-airlines-first-airport-lounges/

Southwest Adds New Airline Partner:
https://upgradedpoints.com/news/southwest-airlines-partnership-lot-polish/

Aruba Marriott Resort Review:
https://upgradedpoints.com/travel/hotels/aruba-marriott-resort-stellaris-casino-review/

What To Expect at Universal Halloween Horror Nights 2026
https://upgradedpoints.com/news/universal-halloween-horror-nights-2026/

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Cruises represent one of the most underutilized opportunities in the points and miles world. In this episode, Chris and Katie cover every way to earn more points on cruise bookings, the best credit cards for cruise spend, how to stack points through airline and hotel portals like Chase Travel and AmexTravel.com, and why cruise line credit cards almost never make sense.

Then the big question: can you actually book a cruise with points, and when does it make sense? They break down the value per point across Virgin Voyages, United Cruises, Marriott, and the brand-new Hilton and Explora Journeys partnership. The honest answer might surprise you.

Plus, Chris shares a car rental story that is a reminder to always film your rental before you drive off the lot.

Best Ways to Book Cruises With Points and Miles:
https://upgradedpoints.com/travel/cruises/best-ways-to-book-a-cruise-using-points-and-miles/

✈️ Learn more at https://upgradedpoints.com/travel/cruises/best-ways-to-book-a-cruise-using-points-and-miles/https://upgradedpoints.com/travel/cruises/best-ways-to-book-a-cruise-using-points-and-miles/

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We've been busy. Let’s get caught up together.

Chris and Katie cover a packed stretch of recent travel including Chris’ stay at the InterContinental Boston by IHG, Katie's American Airlines premium economy flights to Barcelona and Rome booked with Alaska Atmos Rewards points, a Kimpton Barcelona stay through Chase The Edit with a tourist tax surprise, a walking tour of Barcelona, a Vespa tour through Rome, and a Sun Princess cruise specifically planned around a solar eclipse that had other ideas.

Along the way, Chris tests CLEAR Concierge for the first time and breaks down who it's actually worth $180 for. And Katie shares a Chase Sapphire Lounge lesson that will save you from getting turned away at the door

Hyatt Regency Rome Delays Opening:
https://upgradedpoints.com/news/hyatt-regency-rome-central-delays/

What is CLEAR Concierge Service?:
https://upgradedpoints.com/news/clear-plus-new-concierge-service/

Try CLEAR Concierge Free:
https://upgradedpoints.com/news/free-clear-concierge-promo-code/

Is American Airlines premium economy worth it?
https://upgradedpoints.com/travel/airlines/american-airlines-premium-economy/

✈️ Learn more at https://upgradedpoints.com/

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Every points traveler has made mistakes. This episode is our honest debrief.

Before the main segment, Katie shares why Chris convinced her to get the Hilton Honors American Express Aspire Card, how she and her husband both got one on the same day, and why she's already finding it easy to justify the annual fee. Plus, a smart strategy for couples looking to align free night certificates.

Then Chris and Katie go through the points and travel decisions they genuinely regret. Not setting up two-factor authentication and getting an account hacked. Not realizing that points are worth different amounts in different programs. Forgetting about card benefits until it's too late, and so much more

No sugarcoating. Just honest mistakes, real stories, and lessons worth learning before you make them yourself.

How to Use Capital One Shopping:
https://upgradedpoints.com/credit-cards/capital-one-shopping/

$80 Capital One Referral Offer:
https://upgradedpoints.com/news/capital-one-shopping-referral/

Hilton Aspire Card Review:
https://upgradedpoints.com/credit-cards/reviews/hilton-honors-american-express-aspire-card/

How I Lost Out on 65k AAdvantage Miles:
https://upgradedpoints.com/credit-cards/how-i-lost-65k-aadvantage-miles/

How I Lost 90k Delta SkyMiles by Not Reading the Fine Print:
https://upgradedpoints.com/news/not-eligible-amex-sign-up-bonus/

✈️ Learn more at https://upgradedpoints.com/

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