Intro to booking a flight awards with

credit card points or miles

First, I recommend reading this.

***

Starter Flow Chart

● Figure out where you want to go (or a couple places) and roughly
when (or a range).
● Read this guide (or skim it idk).
● Do a few searches using the helpful links towards the middle over
several dates and note down the best options you see.
○ If you’re interested in whether these are good redemptions,
check in the “Some Good Websites” section of this guide for
the links on MilesMastery sweet spots and the Is This A Good
Redemption guide.
● Also look to see if there’s a good cash rate for your route or a
pay with points option that’s viable from your card.
● If you’re having trouble finding a good value, consider more
flexibility.
○ Are you searching middle week which is easier or weekend
which is harder?
○ Do you and your sig other HAVE to fly on the same flight? 1
ticket is easier to find.
○ Can you find a cheaper points flight to/from a hub and pay
cash for a cheap connecting flight?
● If you’re still having trouble, go to the r/awardtravel reddit,
find the pinned weekly discussion thread and post there with:
○ How many people you need to travel
○ Destination, Home airport(s)
○ Dates, date ranges for travel and how flexible you are
 ○ The SPECIFIC (not “some” or “a lot”) amount of points you
have in various credit card systems or mileage/loyalty
accounts
○ Detail the steps you’ve taken above
○ Provide a few examples of flights you’ve found that you
think are the best options
○ Ask very nicely for help
● After that, see what response you get and see if you can take
some advice that’s given if any.
● If still struggling, wait 24 hours then repeat the process of
posting, this time as a top level post on r/awardtravel
○ Ask very nicely
● If that doesn’t work, consider revising your plan.
○ Not every vacation is a good use case for points.
● If it does work, pay it forward by answering someone else’s
question one day.

Frequently Asked Questions

● I see a flight has seats for sale for cash, that means there’s
seats for miles redemption available, right?
○ Nope. Airlines choose when they release award seats, which
partner airlines they release to, how many to release and
when capriciously.
■ This means there’s never a guarantee that there will
be an award seat or several seats or a seat for a
certain price on a certain flight.
● What is the best mileage program/best partner for this credit
card/best program for flying to X place?
○ This doesn’t exist.
○ There are airlines that have certain known sweet spots
SOMETIMES on SOME FLIGHTS over any given length of time.
■ For instance, Air France has some 55k biz class
flights to Europe, AA/JAL has some 60k flights to
Tokyo.
○ Because of the previous question, there is never a guarantee
that a flight is available for miles on the day or number of
 people or location you want AND that’s if someone(s) hasn’t
grabbed that low-cost ticket already
● How do I MAXIMIZE my points/miles from X program?
○ See the above question. This isn’t a thing. Find flights you
want to places you want then try to look in to if there are
good deals.
● I see ____ airline has reward availability for this flight. This
means their _____ alliance partner airline does too, right?
○ Wrong or maybe wrong, airlines only have the seats released
to them at any given time.
○ There’s trends and observable rules one can see about when
this might happen.
■ For instance, Aeroplan gets access to some of ANA’s
flights about a year in advance.
○ Never take for granted that you can book a seat until you
book it.
■ BA Avios are great at booking JAL Premium Economy
which AA can’t book.
■ AA can book JAL Business tickets which BA can’t always
book and for less AA miles.
■ Always search and check to see different strategies
for booking a route.
○ Also, different airlines may cost their partner awards at
different rates.
■ A JAL business class seat may be 60k AA Miles and
$5.60 but maybe 108k BA Avios and $250
● I have miles in _____ program! Can I transfer them to ______
credit card points or ______ other airline program, especially if
they’re in the same alliance?
○ Never. Inter-program transfers are not a thing and the few
that exist (Marriott to Airlines) are almost exclusively not
worth it. If you want transferable points, I recommend
reading my credit card guide linked at the top of this
document. The only other option you have for multiple flight
currencies for the same itinerary is using them to book
different legs or directions of a single/round trip.
● STFU, tell me how I can get to Japan with X Miles!
○ People will be much more likely to help you if you read
something like this guide and find a few options for flights
 and also read around a bit on guides on this sort of thing
that exist on google.
○ It’s much easier to help someone who is already in the
process of helping themselves.

Why should I care?

● Miles cost an airline basically nothing.

○ They choose when you redeem them and they were flying the
plane anyway.
■ You are a seat filler.
○ So you might as well get value from them.
● A lot of times, people have credit card points or airline miles
that are just sitting around.
○ However, points are frequently devalued or lessened with
inflation so your points are losing value or even expiring
sitting there.
○ Thus the term : “earn and burn”
● You could save a lot of money particularly on international or
high class flights.
○ Today I booked a $6,400 dollar business class flight to
Tokyo on the exact date I wanted it for 60k American
Airlines Miles and $5.60. Since it’s a 14 hour flight, this
is very useful since I’d want some form of relaxation as
opposed to a 3 hour flight to Miami or something.
○ Generally, the higher the class of the flight or the farther
the flight is, the more value you get for your miles.
● It’s fun
○ Looking for miles flights, like credit card points, is a
game you’re getting paid to play essentially.

What should I know?

● The price of an award flight is not guaranteed, it is often

dynamic, like the cash price.
○ Just because there are seats to purchase for cash on a
plane, doesn’t mean there will be awards or miles seats on
that plane.
■ A lot less award seats are put out than miles seats,
as you are a seat filler.
■ Also miles availability may differ on different
partner airlines. So AA have miles seats on their
flights you may not find on BA, their one world
partner and so on.
○ The best times to book award flights are generally either
two weeks in advance or one year in advance.
■ Note that different airlines have their own quirks and
particular ways of releasing flight awards.
○ The more flexible you are on where and when you are leaving
or even where you are going to and can connect, the better
the deal you’ll get.
■ For instance, I am currently looking to go to Athens
in September.
● This is a peak time to go so award flights cost
200k points one way in business class.
● However, taking a flight to Amsterdam or Munich
in September is often 55k points one way in
business class.
● Since I’m mostly worried about the transatlantic
journey, I can get a cheaper on miles flight to
one of those hubs and get a cheap cash/miles
economy fare for the 2 hour flight to Athens.
■ Another example, I’m going on business class to Tokyo
in October.
● The best and cheapest miles deal I could find was
going out of Chicago.
● I purposefully check other starting points than
NYC to see if they have good flights since I’m
willing to go to Chicago, Boston, Philly, DC or
even Dallas or Houston for a flight but not to
Cali.
● I got a short flight to Chicago and took the
cheaper business flight to Tokyo
■ This is called “repositioning”
 ■ Generally speaking, if your flight begins and ends
outside the United States, it will be cheaper in miles
and there will be more availability, so consider this
when repositioning.
● If you live in Cali or Texas, consider a flight
from Mexico City. If you live in New York or
Boston, consider a flight out of Toronto or
Montreal.
○ Also consider dates.
■ The busiest days to travel are the weekends and
Mondays. Tuesday and Wednesday tend to have the least
demand so better fares.
● All airline miles are not created equal.
○ Here’s a chart of the technical value of miles, note this
is just a guesstimate, not always true.
○ Also though, many mileage programs have known sweet-spots,
with new ones added or other ones deprecated.
■ For instance, Air France offers their 55k Business
Class flights one-way which are worth about 3-5
thousand dollars, but only for flights that aren’t
well sold yet.
■ American can offer award flights on busy routes or
holidays that cost much less in miles than they do in
ticket prices.
○ There’s also value on “alliance” or “partner” awards where
you use one airline to book another
■ British Airways offers great value on Japan Airlines
Premium Economy or on Qatar Airways to/from the Middle
East. They also offer good value on American Airlines
flights for short-hauls like NYC-Pittsburgh, which can
often be expensive.
■ Virgin can book Air France, Delta or even All Nippon
Airlines to Japan but only when there’s availability.
■ Air Canada Aeroplan can book United, Lufthansa, LOT
and lots of other airlines for discounts.
● There is often, with some exception, no penalty for cancelling an
award flight up to 48 hrs in advance.
○ This means it pays to be bullish on booking as you can often
get refunded the miles.
 ● The best airline mile is not an airline mile at all
○ Credit Card points through companies like Chase, Capital
One, Citi, Bilt and AmEx are generally more valuable than
miles.
○ This is because they can be transferred opportunistically to
programs with the best miles.
○ This doesn’t mean that miles are useless.
■ Some miles like AA are hard to transfer to.
■ Other miles like ANA take a long time to transfer and
so it may be quicker having them.
○ But, for instance, if you book a United flight through the
Chase Sapphire Preferred on Chase’s travel portal, you’d
earn 5x points which can be transferred 1:1 to United.
■ You’d only book 2-3x on this purchase in non-
transferrable United miles on a United branded credit
card.

Stop talking nerd: how do I search for and

book flights?

● Before you look, remember:

○ Be flexible in your dates if possible.
■ Maybe a different date or different day of the week
has a better point value or flight.
○ Be flexible in your starting location.
■ It can be a lot cheaper to fly to Chicago for a 47.5k
Business Class flight to Tokyo than take a 200k flight
out of NYC.
○ Be flexible in your ending location.
■ It’s a lot cheaper to take a 55k flight to Munich then
get an economy flight to Athens then a 200k flight to
Athens!
○ Be flexible in your round-trips
■ It may be cheaper to return from a different location
than the one you started in (like AMS->Paris) and may
also give you a fun chance to see more places.
○ Be flexible in your points and miles
 ■ Don’t transfer from a credit card program until you’re
ready to book.
● Most credit card points transfer instantly but
check to see if they take a while like ANA.
■ Consider a program like AwardWallet or even just a
spreadsheet to track your miles and points.
○ Be flexible WHEN you check
■ Often times checking every few days availability or
pricing might change for a flight.
○ Book quickly: “The PS5 Effect”
■ Many fares you see on these sites will be gone
instantly or very soon.
■ So be ready to book or wait for the next deal
● Free online tools are super helpful. Use them to search for
availability on your days.
○ Seats.aero
■ Great for two weeks out or last minute travel.
■ Shows 7 days of availability on a given route and all
classes available.
■ Very good for city/region to region flights like
Sydney-North America. This is an option other search
engines don’t have!
■ Very fast and gives you direct links to book on the
airline that’s available’s website.
■ No log-in required.
■ Limited programs, so not every frequent flyer program
represented.
■ Only one ways
○ Roame.travel
■ Great for a particular day and airport.
■ Shows almost all airline programs.
■ Shows what credit card programs transfer to the given
airline programs.
■ Pretty fast.
■ Requires free signup
■ Gives links to book through frequent flyer program.
■ Only shows one day at a time.
■ Only one ways
○ Pointsyeah.com
 ■ Allows a 4-day search for one way and shows prices
sorted by lowest or other factors.
■ Requires free sign in
■ Has filters for max taxes paid or percentage of flight
in non-economy classes
■ Has alerts for lower prices if you set them.
■ Shows frequent flier programs, credit cards and
transfer bonuses when applicable
■ Fairly fast
■ One way at a time or Round Trip
○ Britishairways.com
■ Only shows One World Partners like AA, BA, Qatar,
Iberia, etc…
■ Has different availability that isn’t indexed by other
sites.
● They have access to Premium Economy for JAL,
Business on Qatar or Economy for AA that doesn’t
show up on search engines because API access.
■ Multi-day search
■ Slow
■ Relatively low cost to cancel (55 outside 24 hours)
■ Can search one way or round trip
● Round trips may be slightly discounted.
○ United.com
■ Only shows Star Alliance Partners like LOT, ANA,
Lufthansa, Ethiopian, Egyptian…
■ Has 30-day calendar which is helpful with the lowest
price amount shown per day per search.
■ Often a good way to survey a bunch of times.
■ United miles don’t have the best value so not great
for redeeming there.
■ Can see one way or round trips
● Round trips may be slightly discounted
○ AA.com
■ Only shows one world partners like Alaska, JAL, BA,
Qatar, etc
■ Has 30 day calendar which can show lowest miles per
month.
■ Great way to survey a bunch of availability.
 ● Sometimes if a partner flight is available on AA
it may be available on BA which has a worse
search engine.
■ Can see one way or round trips.
■ Many business flights on AA itself aren’t a great
redemption so look out for partner awards like JAL or
Qatar.
○ LifeMiles.com
■ Only Star Alliance Partners like LOT, ANA, Lufthansa,
Ethiopian, Egyptian…
■ Website is insane and mostly broken, sometimes works
in Firefox and Safari but never for me in Chrome
● However this sometimes means deals are available
here that don’t show up on points search engines
like Roame and PointsYeah
● Search is also insane as you have to choose a
route before you choose a date???
■ Also available as an iOS and Android app that is
oftentimes, for some reason, less buggy.
■ Offers several sweet spots like low price saver awards
on United Biz for 80 or 90k internationally.
● Is a transfer partner for Amex, C1 and Citi (no
Chase) which allows them crucial access to Star
Alliance flights, particularly because
Aeroplan/Air Canada has been having issues
lately.
■ Often sells miles for low discount (1.2 cents per
point) making it a good way to also buy some flights
at a discount.
■ Note that they have steep cancellation and change fees
(1-200 dollars) and are not good for multiple
connecting flights.
● Use them for a one way or round trip with no
connections.
■ Can see one way or round trips
● Round trips are not discounted but can be nice
for linking your itinerary in one go.
○ CathayPacific.com
 ■ Only shows one world partners like Alaska, JAL, BA,
Qatar, etc
■ Doesn’t show up (like BA) on other points search sites
but sometimes AA avail for saver or partner awards
means things may show up there too
● This means like BA, this may be a good place to
book One World flights if you don’t have AA or
Alaska miles (which can be hard to get)
● Sometimes has better rates for flights than BA
(worth comparing)
○ Particularly, has good awards to London. A
BA J flight could cost 80k+350 for biz but
only 63k+250 on Cathay!
■ Has weird search which needs you to be logged in and
will only show avail on a 7 days scale at a time.
■ Great way to check against AA or BA availability to
compare pricing.
● CP is a transfer partner of Amex, Bilt, C1 and
Citi meaning that it can be useful for getting
OneWorld flights. Note Chase does not transfer
here.
■ Can see one way or round trips.
■ They are going through a devaluation of their miles on
10/1/23 but I still think it’s good to search there.
○ QatarAirways.com
■ Only shows one world partners like Alaska, JAL, BA,
Qatar, etc
■ Doesn’t show up (like BA) on other points search sites
but sometimes AA avail for saver or partner awards
means things may show up that can’t be found easily.
■ May have lower fees than BA.
■ Has partnership with JetBlue so can get good value in
business on JetBlue Mint, a well respected biz product
with only 10 dollars in fees!
● 38k for Boston to Dublin
● 78k for NYC-LON
○ Google Flights
■ Not for points but great for seeing the value of your
flights relative to cash.
 ■ Generally speaking, accept no less than a 1.5-2 cent
value on your points/miles.
● That said, the best redemption is the one that
helps you when you need it.

Take-aways and caveats

● Sometimes it’s not cheaper to fly with miles. Always check the
price of a flight.
● That said it’s often cheaper to fly this way which is why it’s
super useful.
○ 3-10 cent redemptions are another reason why cash-back
sucks.
● Be flexible! The more people who have to fly together on a
certain day, the less value you get for your miles.
● You get more value for your miles generally on long distance
high-class flights.
○ That said BA, AA and Delta sometimes have good rates on
economy when prices are high due to holidays.
● This guide doesn’t include Airline elite status which sometimes
affects pricing and availability
● It’s easier to get miles from credit cards than flying. Also some
credit cards like Aeroplan and Delta cards offer you a discount
on miles flights.
● When in doubt, ask questions!
○ There’s lots of places like r/awardtravel with answers to
popular questions.
○ Also me, the writer of this doc.
○ Also friends at work!

Some good websites

● Frequent Miler
○ A good blog of miles and travel value spots.
○ Also a podcast.
● r/awardtravel
 ○ Reddit for award travel questions
○ Lots of resources and good award opportunities, especially
for specialized questions
○ It’s reddit, so people may be mean especially if you’re not
following their rules (or just bc) #theinternet
○ Would recommend reading the rules carefully before posting
● MilesMastery Award Sweet Spots
○ This is a really good blog post by a very frequent
contributor to r/churning about sweet spots in redemptions
○ Written 6/5/23 but still quite relevant
○ Answers some good basic “what’s the best x” questions
● How Good Is My Redemption?
○ Good wiki answer to questions about CPP and some good basic
info about general redemptions.
● Lap Seat Award Travel Guide
○ Another good answer/guide by a frequent r/awardtravel poster
on how to book awards for the littlest ones.
● Which Points Should I Transfer To Which Program?
○ Personal thoughts of an experienced award traveler of which
credit card systems to use to transfer to which frequent
flier programs and when to buy points for your awards.
● Easy Non-Aspirational Redemptions
○ Beginners guide to some good first redemptions written by an
r/awardtravel regular on “always there” redemptions that may
cause one to not bang their head too much.
○ Great when you have miles you need to burn or are looking
for an easier paradigm.
● FlyerTalk
○ Old school 1998-level message board of weirdos specialized
experts talking about award travel
○ Don’t post there
○ Can be a good place to google questions though

“Hey thanks for doing this doc dude” and/or

“I hate this crap”
 ● Thanks! I think information should be free, or at least most. I
wrote this so it would make it easier to find info I had to work
to find.
● If you want to say thanks or have a comment:
○ Feel free to send a message or post something nice on the
Reddit post for this.
○ I’m u/dummonger on Reddit if you want to message me
directly.
○ Let me know if you have suggestions for improvements or
something you think should be added
○ If you feel super thankful, feel free to use one of my
posted credit card referrals.
○ Don’t send me any money or anything though! This is free
info! I am not a travel concierge!
○ Also consider if you liked this, helping someone on Reddit
or in your life if this info. Info should be free :)

Appendix A: Consider “Pay With Points”: an

alternate point booking strategy

● This is not strictly an award flight post as is.

○ Since this belongs somewhere in the space between miles and
credit cards, I decided to write this appendix here.
● Sometimes, cash fares are “cheaper” than miles fares or you’re
getting less than a 1.5 cent value on your points.
○ Generally speaking, the “floor” for the use of credit card
points or miles is 1.5 cents per point.
■ You can’t always get this, but greater than 1.5 cents
is what you should aim for.
■ Google Flights is helpful for determining what kind of
value you’re getting as you can price compare the same
flight in cash.
○ Also sometimes it’s advantageous to book cash fares in order
to get more qualifying miles or dollars for airline status
on a particular airline or alliance.
● Also, sometimes you just plain don't have miles in a particular
system or alliance you can use to book a flight.
 ○ This can be true for systems like AA Or Alaska whose miles
can be difficult to transfer to or get.
● In any of these cases, there’s a few systems that have some
version of “pay with points”.
○ This is a way of buying cash fares through a credit card
portal but then paying for those cash fares with points at a
higher than 1 cent per point redemption.
○ This has the advantage of using your credit card points, but
still earning miles on your purchase since you are “erasing
a cash payment” not booking an award ticket.
● For the purposes of this appendix, I am ignoring C1’s pay
yourself back feature for travel or Delta or BA’s “pay with
miles” systems as these are all generally 1 cent redemptions and
I am focused on 1.5c or greater redemptions though I’ll mention a
couple others.
● Different credit cards offer different versions of this.
○ Chase
■ Chase Sapphire Reserve offers a 1.5cpp redemption on
the Chase travel portal
■ Chase Ink Preferred and Sapphire Preferred offer a
1.25 cent redemption on their portal
○ AmEx
■ The Business Platinum card offers a 35 percent rebate
on using points on their portal for all business or
first class flights OR for economy flights on one
chosen airline (the same one used for your flight
credit)
● It’s a little confusing but basically if a flight
costs 1000 dollars and you pay 100k points for it
on Amex’s travel portal, around 4-8 weeks later
you will get 35k points returned to you
● This makes for an essentially a 1.53 cpp
redemption
■ The Amex Business Gold offers a similar 25 percent
rebate
● This is essentially a 1.3 cent value.
○ US Bank
 ■ The Altitude Reserve card offers a flexible 1.5 cent
per point pay yourself back option on any “travel”
category purchase more broadly.
■ This is a little different as US Banks aren’t
transferable but still a good redemption in this case.
● There’s a few good common use cases for pay with points,
○ When the cash fare is cheaper than miles
■ This way the net points you’re spending may be less
than transferring points to a partner.
○ Domestic economy on your chosen airline or domestic
business/first
■ These often have worse redemption rates than other
flights and pay with points may be cheaper.
■ For instance, a recent EWR-LAS first class flight on
United was 676 dollars, 67k United Miles but was only
45k using the Amex Business Platinum!
○ For use on low cost carriers without/limited miles systems
■ For instance, ZipAir operates discount economy and
business flights in a limited market so you can’t use
miles (afaik) to get their flights
■ But 68k Miles/Points (off an $1100 ticket) through the
CSR or Amex Biz Plat may be a better business class
fare than comparable products.
● Moral of the story
○ Always check price and availability on award flights you’re
looking on particularly if you have one of the mentioned
credit cards.

Appendix B: “This is not a hotel award

booking guide”: an even lazier and spottier
intro to hotel award nights.

● Really, this is not a hotel award booking guide

○ That would take a whole other guide.
● Hotels tend to be both:
 ○ Easier to book with points than expensive international
flights
○ Harder to get as high of a cpp redemption than those
international flights
● Also what about Airbnbs?
○ Often cheaper
○ Can use Delta promotion to get delta miles on AirBNBs
○ You can buy airbnb gift cards sometimes on shopping portals
for AA/United and then use those to get miles for the gift
card AND use the delta promotion to get miles for the stay
○ Can code as 3x for travel on some credit cards if paid
directly (like the Chase Ink Preferred)
○ No rewards system.
● Shut up and tell me about hotels.
○ Okay fine here’s a very short summary of SOME hotel programs
and SOME things about them.
● Hyatt
○ Generally speaking the “best” hotel program rewards wise.
○ Hyatt points are worth around 2 cents each on average.
■ On the low end, it can be used to book Hyatt Places
for as low as 3.5k-8k a night which would be
unthinkable in other programs.
■ On the high end, it can book dream properties like the
Alila Big Sur or Park Hyatt Kyoto for 35-45k points
when those properties oftten go for 2-4k a night,
giving them around a 6cpp or more redemption.
● However these redemptions are often sold out for
that reason.
○ Bilt and Chase transfer 1:1
■ Some people think this is the best use of Chase
points.
○ They have a good 95 dollar personal credit card that gives
you a free night every year.
○ They have a decent business card which helps you earn
status.
○ The highest status at Hyatt (globalist) is hard to get
(requires 60 nights a year) but is quite valuable
■ Comes with free nights, free parking, free
breakfast/booze, possible suite upgrades
 ■ Other tiers of status not as valuable
○ Mostly notable for the high value of their points, the
general quality of their properties and the 1:1 Chase
transfer.
■ Also notable for some all inclusives and resorts in
the Caribbean.
○ There are generally less Hyatts than some other brands
though.
● Marriott
○ Some good properties. Lots of good credit cards.
○ Transfers 1:1 from Chase or Amex.
○ Points vary wildly in value but usually worth .5-1.1 for cpp
which isn’t great.
○ On the low end, could book Moxys (hipster hotels) or Four
Points (biz hotel) for cheap cash or points
○ Mid-tier there’s a lot of options from Sheraton to Marriott
to Courtyard etc…
○ High-tier includes the Ritz-Carlton brand which is pretty
famous.
○ Mostly well regarded with large footprint
○ Hotels tend to be nicer outside of America and also you get
better value for points
○ Mostly notable for many credit cards that offer free nights
or points bonuses which make booking awards fun/possible
■ They have a 95 dollar card which comes with a free
low-tier night every year and 5 mid tier night for
signing up
■ They have a 600 dollar card which comes with an
expensive free night cert every year and a bunch of
points and some perks like Platinum status.
■ If getting one of their cards definitely do some
googling as they have insane rules on which ones you
can get when.
○ Not a great transfer partner from either AmEx or Chase given
points general low worth
■ Sometimes there are transfer bonuses though.
○ Offers a 5-for-4 points bonus where you get 5 nights for the
points price of 4 which can be a good way to get value
■ Doesn’t work for free night certificates though.
 ○ Large global footprint but hotels vary in quality so make
sure to check Google reviews.
● Hilton
○ Some great properties and some crappy ones. A couple good
credit cards (mostly one).
○ Transfer 1-2 from Amex (still not a great value as Amex is
generally valued at 2cpp)
○ Many low, mid and high tier options
■ Ranging from Hilton Garden Inn (low-tier)
■ Hilton and Curio Collection (mid-tier)
■ Waldorf Astoria, LHR(high-tier)
○ Very large global footprint
○ Points are famously not worth much (.5cpp)
■ However, oddly as you get towards higher tier
properties, points can veer closer to 1cpp or higher.
○ Their free night promotions (one comes with their Hilton
Aspire credit card) are quite strong because unlike Hyatt or
Marriott, you can book ANY tier of hotel with a free
standard room available with them.
■ This means I personally have redeemed a free night for
a 1200/night property. Quite nice.
○ Speaking of free nights, they have the Hilton Aspire card
for 450/year from Amex.
■ Comes with one of those nearly unlimited free nights.
■ 250 airline fee credit (easy to use)
■ 250 Hilton resort credit (not terrible to use)
■ Hilton Diamond status (the highest available)
■ Pays for itself quite easily
○ Also have the same 5-for-4 promotion as Marriott which can
be quite valuable.
○ Mostly useful for any free night or 5-4 promotions.
● Lightning round (all the others I don’t want to talk about.
○ IHG
■ points can have good value sometimes and some good
properties (but many crap ones)
● I hear the Kimpton and InterContinetal brands are
nice.
■ With one of their credit cards you can stay 4 nights
on points and get 1 of them free (4-for-3)
 ■ Sort of an up and coming program.
■ Chase transfers 1:1 to IHG which is an ok deal
sometimes.
■ I hear their credit cards can be ok.
○ Wyndham
■ C1 transfers 1:1
■ Only really notable for two things:
● Their business credit card which enables a crazy
cruise matching scheme
● Vacasa rentals (like airbnbs through points)
which can book quite nice rental properties for
15k a night that can cost 350/500 a night.
○ Choice Hotels
■ Idk I never use them.
■ Hear Citi transfers 1:2 to them.
■ Apparently have some good international properties,
especially in Asia?
■ They own Best Western and Comfort Inn in the US so be
aware they may be some lower tier properties.
● Ways to search for availability
○ I usually just go to the hotel programs site or app as most
of them are well developed and there’s less choices than
airlines
○ There’s also:
■ Maxmypoint
■ Rooms.aero
■ Awayz
■ Bilt Hotel Search
○ Good for monitoring hard to find properties across different
programs.
● Takeaways
○ Hotels imo aren’t the best use of points all the time
■ Rates also tend to go up for families sharing a room
etc
○ However, you’re going to spend more time in a hotel than a
plane usually.
■ So it may behoove you to use the points so you can
stay somewhere decent.
 ○ Hyatts and 5:4/4:3 deals can offer good transfer values from
cards.
○ Always do the math and see if you're getting good values for
your points/certs.
■ Also check against local airbnbs?
○ I’d personally recommend never using travel portals (Expedia
etc) or credit card portals to book hotels
■ Hotels are much more sensitive to this sort of things
than airlines and often won’t give you points if this
happens.
■ Exception generally is AmEx’s FHR benefit through
their Amex travel site may give you Hilton or Marriott
points since they are connected but it isn’t
guaranteed.
○ Always check to see what current hotel promos are and take
advantage if possible of good hotel credit cards like the
ones mentioned here.

Appendix C: An even lazier and less formatted

guide to which domestic airline to pursue
status with.

All of the following are based on full fare domestic travel (with the
desire for international aspirational travel) and are my opinion only.
Prepare for a lot of the word “mid” and “middling” but mostly because
I am lazy and they are appropriate to the subject matter.

AA miles are theoretically worth the most but AA experience on not

major routes is bad. Also AA lounges are hard to get into without an
expensive ticket or one expensive card. Their status is also easier to
earn through cards and shopping portals and is middling useful
generally at low levels. Lounge access at mid status/ international
lounges but one world is a smaller alliance than the others imo where
I have traveled. They do let you select main cabin extra which can be
slightly better with some status.
UA has a middling domestic inflight experience and decent lounges that
are sometimes accessible depending on class/cards but the best network
of partners for international travel. Its miles are sort of middling
but still get good value internationally just not as big as AA. Their
status is relatively expensive to earn and has middling value as it
doesn’t get you into their own lounges without business class fare.
Their united club is fine and their Polaris (only long haul intl)
lounge is excellent but hard to get into. Mid status can provide some
good value for intl lounges though on partners and Star Alliance is in
Asia, Africa and Europe where a lot of travel is. They do let you
select “Economy Plus” (slightly nicer seats) with some status.

DL has the best domestic inflight experience (imo) and great lounges
which, even with tightening restrictions, are the easiest to get into
with a regular ticket and a card. However, their miles are very low
value without hacks (non-us redemptions on partners) or middling value
with their credit card. For status, they are the best imo at getting
you upgraded on their flights to first/business even at low levels but
don’t have great international benefits necessarily outside of their
big 3 SkyTeam: Virgin, AF/KLM and themselves. Also status can be
gotten with no flights and two credit cards as of Jan 2024.

Alaska imo has a pretty crappy inflight experience (no screens, no lie
flats in business) and pretty chill though no frills lounges. They are
however in one world like AA, earn good miles on their flights that
can be redeemed internationally and are relatively easy to get status.
Lounge access is bad and isn’t affected by cards I believe. They are
only really useful as a west coast airline and I think of them in the
same breath as JetBlue or Southwest, not mentioned here as they have
low mileage and no real international partners.

TLDR:

For most people:

don’t chase status, you usually don’t fly enough. Take whatever is
cheapest and get lounges from a credit card like Amex Platinum or CSR.
For those who fly a lot domestically for work and have families that
want to take on domestic trips:

go for delta imo as long as it’s a hub. Good lounge access, good main
cabin redemptions with a credit card of theirs.

For those who fly a lot for work and want to fly internationally for
free:

Go for AA or UA depending on who flies to your hub most easily and

where you plan to travel (also whether you want to do shopping portal
hacks on AA)