This newsletter was previously sent on October 27, 2025
Estimated reading time: 9 minutes
Good morning!
Last week, I asked how much you would value the free night certificate at the Waldorf Astoria NYC. It saved me $400 in cash on a hotel I would have booked (Courtyard/Hyatt Place-type hotel), but instead I was able to “splurge” at the Waldorf Astoria in a room that was listed for $1,600. Here were the responses! The plurality voted for $400 in value.

Now let’s get into the highlights.
This week’s highlights
- Set a plan to maximize holiday spending + tax season for SUBs
- A gift (in the form of a lounge) for Chicago (ORD) travelers
- Hyatt 4Q promo is a bag full of treats?
- Use points for experiences!
- ANA first class bookable on Air Canada again?
- Deal of the week
- Other news to highlight
Set a plan to maximize holiday spending + tax season for SUBs
Wow, time flies and it’s almost November already. The November-December period is the probably the best time to buy stuff as retailers offer seasonal promotions, summer clothing is discounted, and cashback portals have elevated offers that stack with these promos. This is a good time to plan opening a new card(s) to meet minimum spend and get those sweet sign up bonuses (SUBs). Also it’s the time of year to think about paying estimated tax as 4Q estimated tax payments are due January 15.
With these 2 factors at play, you might be able to hit higher minimum spends this time of year, allowing you to open up other cards you may not have previously considered.
Anyways, cashback portal Rakuten dropped a sneak peak at holiday deals to kick off the season. I’m going to take advantage of Ulta, Dermstore, and Lululemon for sure (I am a basic b*tch). No major rush as Thanksgiving through Cyber Monday will also have elevated cashback at many of these stores too.
Anyways, back on the topic of planning, Rakuten cardholders (Rakuten card link, not a referral or affiliate) will get 30% cashback on the below retailers too including on hotels on Expedia. Could you potentially time it to switch payout to Bilt points (Frequent Miler) if that is launched soon?
Anyways, if you still don’t have Rakuten, it’s essentially free money for shopping online in return for giving up data for ads (you already give it away for free anyways), you can sign up with my referral link and you and I will both get $50.

A gift (in the form of a lounge) for Chicago (ORD) travelers
I fly through Chicago (ORD) a lot. So much that I opened up a United Club Card for lounge access. For those who have any of the premium credit cards and Priority Pass, you’ll know that Chicago is a dead zone for lounges that previously only had the Swissport lounge in T5, which is certainly NOT worth a visit to (The WSJ calls it the saddest airport lounge in the US). However, for those who are flying out of, or don’t mind going to T5, Air France is here to save you (except between the hours of 12pm to 5pm).
Air France’s new ORD T5 lounge just opened and is part of the Priority Pass network (details here on Priority Pass site). The lounge will be generally be reserved for Air France/KLM passengers between 12pm-5pm though, so you will likely need to visit outside those hours (5am-12pm and 5pm-8pm).
The new lounge looks gorgeous, with the signature Oxford Blue color throughout. Plus, the upholstery should be fairly new. Check out pictures and more details here (One Mile at a Time).

For those who haven’t experienced Swissport, don’t go. Especially if you are not even in T5, as they somehow turn people away for being too busy! Paying business and first class passengers used to be subjected to it before the LOT Polish lounge opened in December 2024.

Hyatt 4Q promo is a bag full of treats?
Hyatt’s 4Q promo is probably better than what Hilton and Marriott are offering. It seems like the offers are targeted and the one I got is a free Category 1-4 hotel certificate with a 2-night stay. I also got 2x points on dining at Hyatts in Japan and Guam. The free Cat. 1-4 certificate offer definitely beats 2,025 Marriott points per stay or Hilton’s 1,500 2,500 points per stay…
Make sure to sign up directly on Hyatt’s site or app with just a few clicks. People may have different offers including 2-3x points on stays.

Use points for experiences!
Don’t forget, points & miles can be redeemed for other things besides hotels and airfare. You could cash them out for gift cards (bad value), statement credit (could be useful), or even for unique experiences. Most experiences are redeemed through an auction process. Check out some of these below!
- VIP Guinness Experience + Stay in Dublin (Marriott Bonvoy Moments)
- Hospitality Tickets for Commanders vs. Dolphins in Madrid + Hotel on Nov. 15-17 (Marriott Bonvoy Moments)
- Lower-level tickets to Jets vs. Browns on Nov. 9 (Marriott Bonvoy Moments)
- 2x Suitebox tickets to Nets vs. Pistons on Nov. 7 (Qatar Privilege Club)
- 2x tickets and 2 night stay in Ann Arbor for Michigan vs. THE Ohio State (Hilton Honors)
- Pair of tickets to Moulin Rouge! The Musical in NYC on Nov. 13 (United MileagePlus Exclusives)
- EXPIRED but could come back: World Series tickets using Capital One Miles or Cash Back. C1 cardholder exclusive! (Capital One)

ANA first class bookable on Air Canada again?
Air Canada Aeroplan is a really great award program – at least on the redemption side. In addition to being able to book Star Alliance partners (United, Lufthansa, Austrian, EVA, ANA, etc.), there are some unique airline partnerships that you can also redeem for. This includes Air Serbia, Emirates, Etihad, Gulf Air, and Oman Air. They also sometimes have more availability to book Singapore Airlines business class that isn’t released to other Star Alliance partners. Let’s ignore the rates to book Emirates and Etihad business class and talk about ANA.
Aeroplan (or potentially the partner airlines) has been wishy-washy on releasing awards on certain partners, including not releasing space to book ANA first class. ANA business class used to be blocked off from booking as well, but that has luckily returned and has been more permanent. The last time I recall seeing ANA first class bookable through Aeroplan was July 2024, but I guess it is potentially back for now?

Also is it even worth it to use Aeroplan to book ANA now that ANA allows one-way bookings? Well, it depends. Given ANA’s pricing depending on low, regular, and high season. First, only Amex points transfer directly to ANA and it’s never instant (usually 3 days). So if you don’t have Amex, your options are limited. Second, ANA can charge up to 150k for a one-way ticket while Aeroplan would charge 110k+ for the ticket (126k is fully refundable option) if it is high season. Third, you’ll want to check when the flight is, as if it’s within 331 days of travel you’ll want to use Virgin Atlantic to book.
More details on how to find and book ANA business and first class awards can be found on my blog here.

Deal of the week
Qatar is still releasing award space 361 days in advance. You can book 2x Qatar business class seats between the US-Doha starting at 70-94.5k points one-way depending on peak vs. off-peak pricing. Combine with Chase 30% bonus to British Airways (which move freely to Qatar Airways). Notably, pricing can change (for the better actually) depending on your final destination. Use this to your advantage and plan your 4Q26 trip.
Tip: FYI, last year, Qatar started blocking the ability to book business class awards from December 15 through Mid-January. Blackout dates can change at any time though and Qatar can release awards during prior blackout dates later (June-July 2026 has dates now that were previously blacked out).
See the below example. Even though the IAD-DOH segment is during peak season, if you connect onward to Hong Kong, you will not be charged peak pricing for the trip and will pay the usual 95k saver award cost. However, if you fly just IAD-DOH, you will be charged peak pricing of 94.5k points one way.


Other news to highlight
- Chase Sapphire Reserve new benefits are live (Doctor of Credit)
- United and JetBlue partnership not so great to start (Frequent Miler)
- Bilt Cash program replacing Milestone Rewards on Jan. 1 2026 (Bilt)
- Omaha to get its first airport lounge in 2027. Big win for my bro! (Build OMA)
- Southwest’s new boarding plan + procedures (Wall Street Journal)
- T-Mobile ends autopay discount loophole (Miles Talk)
- Hilton “improves” their 4Q promo (One Mile at a Time)
- Chase 20% bonus to Southwest (One Mile at a Time)
- Delta Air Lines, Inc. vs. Marriott International, Inc. over Delta Hotels (View from the Wing)
- Book AA business class saver awards between JFK-TLV, starting at 75k (Dan’s Deals)