Award Booking Artistry


a man holding a paper and a picture of a man

Getting the best deal on an award ticket is rarely done by going to one airline’s website and searching round trip. On this week’s Frequent Miler on the Air, we discuss the artistry that goes into building a masterpiece of a booking. From using partner miles to leveraging stopover perks to skiplagging and more, we give you a glimpse at our palette. Sure, it takes time to do all of these searches, but you you can’t rush good art.

Read on for more from the blog this week about what you need to do right now to get yourself ready for the coming Marriott changes, upgrade strategy regarding the IHG credit cards, your entry point to get back on the status-match-go-round again, and more.

1:28 Giant Mailbag
5:57 What crazy thing did Radisson do this week?
10:17 Mattress Running the Numbers: Should you product change to the IHG Premier? 26:58 Main Event: Award Booking Artistry
31:47 Mixing and Matching Airlines on a single trip
33:38 Look at other International Gateways
36:30 Look at using partner miles
39:11 Throw-away return tickets
43:42 Skiplagging
47:25 Nested Trips
51:27 Alaska stopover rules

53:41 United Excursionist Perk
56:37 Leveraging off-peak pricing
1:00:00 Upgrades
1:03:48 Post Roast
1:09:47 Question of the Week: What’s up with the American Airlines eShopping portal?

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This week at Frequent Miler

Developing a British Airways strategy for business class flights using points

British Airways Airplane

Some of the inspiration for this week’s show came from this post about how I was looking at using a bit of creativity to figure out the best way to get to Europe twice this year for trips I have tentatively booked. In this post, I look at the possibility of booking British Airways Premium economy and upgrading with Avios. Unfortunately, it isn’t clear whether I could do this entirely with points, but if I could this would certainly be an intriguing option.

My nightmare booking Preferred Hotels via Choice

a man standing in front of a beach

Greg is a glutton for punishment. If a sum total of 7 hours on the phone between initial booking, changing dates, and adding a second booking sounds like a good way to spend your Saturdays, then Greg has the sweet spot for you. Booking Preferred Hotels through Choice is a great example of the time we sometimes have to invest in this game to get a great deal, but if you enjoy the thrill of the hunt as much as you do staying in a swanky place with a pittance of points, this is the post for you.

Best uses for Marriott free night certificates 🆕

a balcony with a view of a grass field and a sunset

If you have Marriott Bonvoy free night certificates, now might be the time to book some of these best current uses of free night certificates. Sometime soon (likely in March), Marriott will begin pricing awards dynamically. Also soon (and nobody knows for sure when), Marriott will debut the ability to add points to a free night certificate. While that will certainly increase the flexibility of your certificates, you can bet it means that most of the properties on this list will suddenly cost you a certificate and points — so book these now while they only cost you a certificate.

Marriott Platinum Elite Free Breakfast Simplified

a plate of food with bread and tomatoes

So you want to use your free night certificate and get free breakfast? Well, for the latter part of that, you’ll need to consult a chart or two or three to figure out whether or not your elite status can get you a bagel or some eggs. With Marriott’s wide assortment of brands and distinctions between hotels and resorts and exceptions to the rules, it’s hard to know what you’re going to get without consulting this resource in advance. Bookmark this one to come back to it when you’re making a booking.

Got a Marriott Travel Package? You might not want to attach it.

a man holding a stop sign

While it’s time to make your move on using most types of Marriott free night certificates, there is one certain exception: Marriott Travel Packages. These 7-night certificates are no longer available for purchase, but if you’re sitting on one of them your best bet is probably to wait until Marriott cancels it and replaces it with enough points to book 7 peak nights at your chosen category level, then book what you really want. If you have a property in mind right now that you expect to jump way up in award price when categories go away, it might make sense to lock that in now by attaching your certificate, but otherwise it’s time to hold off. On the other hand, if you have your certificate already attached, you probably just want to leave it alone lest you risk getting it cancelled and replaced with just 5,000 points as per Dan’s story (linked within the post).

New additions to the Best Offers page

close-up of credit cards

Any time you think you’ve already gotten “all of the cards”, there are probably at least a few (dozen) more that you haven’t yet nabbed. This post outlines hot takes on a few that we recently added to the Best Offers page, a couple of which could certainly be intriguing depending on your situation.

It’s time for a new IHG credit card strategy

a bus with a logo on it

During this week’s Mattress Running the Numbers segment, Greg and I talked about whether or not it makes sense to upgrade the IHG Traveler and/or Select cards to the Premier given the new set of benefits that have been announced. In this post, Tim talks it out for himself in terms of what to do now. I stand by my argument on the podcast: if you have the Traveler card and you weren’t already interested in the Premier’s free night certificate, you can probably sit tight with the Traveler card; if you’re already paying $49 a year for the Select, I think it’s worth $50 to unlock more potential value from the free night certificate, get $50 in United credit, and trade the 10% rebate for the 4th night free. That is true unless the Select card’s free night certificate turns out to be upgradeable with points, in which case I’d gladly stick with the reduced fee. Guess we’ll see!

(Update: Warning) The Motley Fool: Save 50% With Amex Or Citi Offer Or Earn 7,400 AAdvantage Miles & Loyalty Points + More

a yellow triangle with a black exclamation mark

I’m including this Quick Deal post this week just as a warning for those who might have seen the original post and missed the update: The Motley Fool seems quite focused on making sure that people don’t stack the several concurrent marketing campaigns that they are running through different channels, so this offer probably isn’t worth considering unless you don’t intend to use the best credit card to pay for your subscription.

Match Hyatt status to MGM Rewards again

Reminder: Match Wyndham Status Back To Caesars Rewards

jetblue blue flex

It’s that time of year: Don’t forget to get back on the status match-go-round. I made sure to match my statuses around so that I have them in case they come in handy and so that I’m prepared to match back when the next status level drops.

That’s it for this week at Frequent Miler. Keep your eye on this week’s last chance deals to get before they’re gone.

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Points Adventure

This has to be the best image yet. Love the fun and silliness of them. It’s great to laugh in addition to the great content.


Just wanted to say, great picture of Greg! Much love for the Bob Ross reference

Dave Hanson

Nick, you write,

I stand by my argument on the podcast: if you have the Traveler card and you weren’t already interested in the Premier’s free night certificate, you can probably sit tight with the Traveler card; if you’re already paying $49 a year for the Select, I think it’s worth $50 to unlock more potential value from the free night certificate, get $50 in United credit, and trade the 10% rebate for the 4th night free. That is true unless the Select card’s free night certificate turns out to be upgradeable with points…

I disagree–unless the cardholder (a) does not already hold a premier or Traveller card too, and (b) has no interest in or ability to get such a card before the March 24 conversion date. Here are some reasons why:

  1. IREVERSABILITY. We have every reason to believe you can convert Select-Premium at any point down the line–but you can’t undo that decision once made. With this much in flux, why not wait to see how the variables shake out here?
  2. LIKELY INCREASED VALUE OF 10% BENEFIT. On the podcast, you noted that you and Greg don’t redeem many IHG points for stays, minimizing the value of the 10% back benefit. Fair enough. But even if only the Premier’s free night certificates turn out to be upgradable with points after March 24, won’t that upgradability make it that much more likely that you *will* redeem more points (if only for those upgrades), increasing the value of the 10% rebate?
  3. FUTURE CC “UPGRADE” OFFERS. Many select cardholders have already been offered 5k points to “upgrade” their cards Select->Premium. If Chase really wants to sunset the Select card, I expect to see these or even more generous offers going forward. Why do now for free what they have and likely will bribe you to do? 🙂

No question, the significant enhancements of the Premier card will make it more attractive for most than will a Select card alone. But because their benefits are stackable, the combination of the two has long been much more attractive than either alone–and the Premier’s enhancements will only increase the value proposition of that combo.

Dave Hanson

I appreciate the thoughtful reply Nick.

It sounds like we agree on the key takeways. Specifically, if you DO have a Select or Traveler card, DO NOT have a Premier card currently, AND aren’t willing or able to open a new IHG Premier, THEN the enhancements to the Premier card are attractive enough to likely merit an upgrade–IF the select card’s annual free night remains non-upgradable, and hopefully with the added appeal of a non-trivial upgrade bonus.

I am puzzled as to why you see yourself *only* redeeming points for upgrading the free night, though. If you go all the way to the Maldives, to use your example, surely you’ll stay more than one or two nights, meaning you’ll want have to book additional nights on points, no? So then you won’t just get back 10% of the points used to upgrade the certs, but also 10% of the entire amount used for those additional days.

You’re probably right that we won’t see better upgrade offers from Chase. But I’d rather take $25-30 in points than $0. 🙂 More significantly, unlike in the other cases you cite, the stackability of these two cards’ redemption benefits give Chase / IHG a greater incentive to encourage conversions versus letting folks hang on to two cards indefinitely.

Bottom line: I’m glad you’re not converting until after we see what’s what post 3/24. And I wonder if the upgrades to Premier will incline you and other travel hackers to consider redeeming more points going forward–which makes keeping the Select / Premier duo that much more attractive.

George the Blogger

More pictures of Nick would be nice though.

George the Blogger

Please cut down or eliminate the silly and quite frankly “turn off” pictures of Greg mugging throughout the posts. It not only adds absolutely nothing to the great content but also reminds me of Emily MMS.

Ed Kent

Personally, I like the sense of humor these photos show. The subtle and not so subtle silliness is entertaining and gets people’s attention without being vulgar or offensive. Clean fun. This whole hobby is about enjoyment and the site and content reflect that. The rough photoshop type image of him as the painter most of us know from years of PBS, was not meant in an offensive way, but in light humor and sure… silly. Why not have some fun?

Mick Dodge

yes i agree up until it becomes too campy, then it becomes annoying……….Remember MILLION MILES SECRETS, pictures of Emily. FFM is on the verge and I am here to help. I would start with more Stephen Pepper! I have a picture of him in my bedroom right next to my Farrah Fawcett swimsuit poster.