Booking Hawaii: Part 1 – Flights for 4 to Honolulu

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Next month, I’m headed to Honolulu with my Mom, stepdad, and little brother. I’d been throwing around the idea of a family vacation for a while.

I haven’t been back to Hawaii since 2013.

I enjoyed my time at the Hilton Hawaiian Village so much, I swore I’d go back someday. And now that I’m all Hilton-y and have Diamond elite status, I thought my Mom would absolutely love staying here with me. So I wanted to treat her to a trip.

Nothing quite like a Hawaiian sunset

Nothing quite like a Hawaiian sunset

But first, to get there.

Sussing out flights to Honolulu

So rich was I with Citi ThankYou points that I looked into all the booking options:

For added fun, I also looked at flights from the West Coast. Because you can pay 12.5K Avios each way for flights on American or Alaska – and I had plenty of Chase Ultimate Rewards points. I even checked into award flights on United thanks to increased award availability for having the Chase United Explorer card.

The first snag was that me and Jay (who ended up not being able to go – more on that in a later episode) wanted to fly from Dallas. And my Mom and stepdad had to leave from Memphis.

I wanted to line up the flights to:

  • Arrive at similar times in Honolulu OR
  • Connect in the same place so we could fly together
  • Have specific travel dates

This was gonna be tough.

I thought we could all meet in Denver to fly on United. Or LAX to fly on Delta. Or Phoenix, maybe, to fly on American. I tried every combination I could think of.

Here's the award space for ONE person

Here’s the award space for ONE person

Finding one seat was a piece of cake. Finding two, sure.

Finding four to arrive on the same day… not so much.

I searched for a couple of hours to make several dates work. We were all flexible.

On a lark, I checked paid fares and noticed they were pretty cheap right after Labor Day from Phoenix to Honolulu non-stop on American.

To fly from Dallas to Phoenix is cake (both are American hubs). And lo and behold, 2 award seats were available from Memphis to Phoenix to catch the flight – but only in First Class.

So turned the little gears.

Putting it all together

In the end, using Citi ThankYou points for paid flights was the best deal. We got the exact dates and flights we wanted without having to worry about award availability.


~30K Citi ThankYou points for each round-trip flight from Phoenix to Honolulu

All of these are from Phoenix to Honolulu. I am staying 5 nights and my Mom and stepdad are staying 4 because they had to keep an eye on their vacation days.

Fares for Jay and me were ~$478. And fares for my Mom and stepdad were ~$530.

Had I booked award flights, I would’ve paid a very similar amount of points. Again, I can’t overstate how simple of a solution this was.

Find the flights, pay with Citi ThankYou points – done. No more searching. Booked.

I'm coming for you, Honolulu

I’m coming for you, Honolulu

It was especially convenient given the way we wanted to structure our dates and flights. This would’ve been much harder to book as a regular award. Not for one or two, but for four… yes.

Booking this trip has made me love Citi ThankYou points even more. So I’m disappointed they’re reducing the  value toward American Airlines flight for Citi Prestige cardholders from 1.6 cents each to 1.25 cents each next year.

Put in perspective, these flights will cost ~38,000 and ~42,000 Citi ThankYou points, respectively, next year.

That increase adds up fast. I’ve done well with this particular perk, so I hate to see it go. Ah well, another year to enjoy it.

But wait, what about getting to Phoenix?

Oh yeah, that detail. After I booked the main flights with Citi ThankYou points, I wiped out my balance. Earn and burn, I always say.

So here’s what we did. Jay and I bought a cheap positioning flight. They were ~$150 each. Not worth redeeming miles or points for.

My Mom and stepdad’s flights were tougher.

For serial?

For serial?

Non-stop flights were expensive (and only available on American – I didn’t want to make her connect again). To make it harder, American was only releasing First Class award seats.

But then I thought…


I have a lot of these points too.


You can book American award flights with BusinessExtra points

I usually let them accumulate, and then treat myself to a free Admirals Club lounge membership whenever my current one runs out.

I had about 10,000 of these points, so I figured why not put them to use to fly my Mom in First on her way to join me in Hawaii?

As soon as I redeemed, I got an email with the award code. I called the number in the email, fed the agent the flights, and had it booked in 5 minutes. Seriously so easy.

~$11 for First Class tickets? BOOM

~$11 for First Class tickets? BOOM

The agent charged me $5.60 each way, so it came to about $22 for both tickets.

Ode to Citi Prestige

You beautiful thing. Why must you change?

Why YES, I can work an Excorcist ref

Why yes, I CAN work an Exorcist reference into a “Booking Hawaii” post

On July 23rd, 2017, my favorite card, the Citi Prestige, will get a little less shiny. Specifically:

  • No more Admirals Club access
  • The 4th night free will be an average cost of the 4 nights, taxes excluded
  • Points will be worth 1.25 cents each toward flights, instead of 1.6 for American Airlines and 1.33 for others
  • No more free rounds of golf

You’ll still get:

  • $250 annual airline credit
  • 3X on airfare and hotels booked directly
  • 2X on dining and entertainment
  • Priority Pass Select membership

I booked this trip with the 1.6 redemption perk. And, you’ll soon find out, I paid for 4 nights but will get the 4th one free. And even topped off my Hilton balance to get another free night. So this card had a huge hand in planning this trip (hence my ode).

The good news is, you still have close to a year to take advantage of all this.

Apply before September 1st, 2016, and you’ll get Admirals Club access through July 23rd, 2017. Apply after September 1st, you won’t get in.

It’s got a $450 annual fee, but considering it’s August, you can get $250 in airline credits for 2016 and $250 in 2017. By the time the changes kick in, you can reassess whether or not you want to pay again.

Yep, this card is still worth a small pile of cash

Yep, Citi Prestige is still worth a small pile of cash

Either way, you come out ahead financially and still get all the other perks. You’ll also get 40,000 Citi ThankYou points when you spend $4,000 in the first 3 months of account opening – that’s worth $640 toward American Airlines flights (including partner codeshare flights).

So yes, you can very much come out ahead with this card. I say right now’s the best time to get it if you’re ever going to.

To apply, click here, select Citi, and you’ll see it right on top.

Bottom line

This was first time planning a trip for 4. And to all you families out there, mad respect. I don’t know how you do it.

In total, I paid:

  • Exactly 126,000 Citi ThankYou points for 4 round-trip coach tickets from Phoenix to Honolulu
  • 6,400 BusinessExtra points and ~$22 for 2 round-trip First Class award tickets from Memphis to Phoenix for my Mom and stepdad
  • ~$300 to position Jay and myself in Phoenix from Dallas

It always hurts a little to redeem that many points at once.

But the beauty of redeeming points this way was being able to throw out ALL of the award charts. I found the flights I wanted and had them within minutes.

That allowed me to work through the snags and select my own dates, meet my Mom in Phoenix, and take the family on a trip to Hawaii.

I’m so excited for this trip. Next up, adding my little brother into the equation and booking the hotel stay.

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About Harlan

Just a dude living in Memphis, traveling, and working toward financial independence.

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  1. I’ve never seen Business Extra rewards before. Looks very interesting, but I assume not really talked about much because of high annual fee?

  2. what is cancellation policy when using TY points to purchase AA flights? Do you get your TY points back is you cancel?

    • Great, great question.

      What happens is your flight is treated like any regular AA fare. So you’ll get credit with AA based on the value of the flight – AND you will have to pay AA’s exorbitant $200 fee when you use the credit in the future. You never get your TY points back. Once they are redeemed, you have to deal with American’s policies.

  3. The PHX-HNL 757 is crap . I’ve used the AS boa companion 3xs from ORD . Have gone to OGG and HNL on newer 737 with exit row seating is pretty comfortable . Goal being total cost $800 for 2

    • Wow, that’s a good deal from ORD!

      I know the plane will be crap, but it was free thanks to Citi TY points on AA metal. I’m psychologically preparing for it lol. Hoping to get on and pass out lol. At least it’s only 6 hours from PHX.

      Would LOVE to use my AS companion pass like you did. *ideas*

      • Use ita matrix for fares that should be around 625 4-5 nights makes sure they are not R fares if you try to credit them to AA. it sucks the earning is t 1:1 anymore. At least that fare is the magic number from ORD . Only problem is unless it’s Seattle may require an overnight stay to a west coast hub. Safe travels .

        • Sweet, thanks for the tip. Yeah, sucks about the crediting percentages to AA now. :/

          Ah well, can’t beat a cheap trip to somewhere beautiful. 🙂

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