Booking Hawaii: Part 2 – Using Citi ThankYou Points for Award Flights on Delta and United

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When last we parted, all was happy and good. Flights for 4 people were booked to Honolulu. Then life, as it does, got in the way.

Jay went back to New York for a too-good-to-pass-up film job. That’s right – I am now in Dallas alone. *cue torrential tears*

That was a whole other wrenching experience, but it also had consequences for this planned trip.

“So no Hawaii trip?” “I can’t.” Crap.

No Honolulu for you?

No Honolulu for you?

I called Connexions Loyalty (the travel agency Citi uses to book flights with ThankYou points) to ask if I could transfer the ticket to my little brother. I knew it would be a long shot, but worth trying.

The best they could do was cancel the ticket and give Jay the credit – no transferring, no name-changing. Oh, and there would be a $200 fee to redeem the credit. That stung, but at least part of the ticket will be put toward eventual travel.

By the time this all shook out, I accumulated more Citi ThankYou points. And continue to earn 30,000 to 40,000 ThankYou points per month.

Then I thought, why not take my little brother anyway?

How to add another person to the trip?

By this point, coach flights from Memphis to Honolulu were nearly $1,000.

Too many pernts

Too many pernts

That would cost about 60,000 Citi ThankYou points and… no way! I can do better.


No cigar, either

The original PHX-HNL trip the rest of us bought, was still available for ~$478 round-trip, or about 30,000 Citi ThankYou points.

While that was helpful to disregard award availability for 4 people, I’d still have to deal with the Memphis to Phoenix segments. Which would of course cost more points.

So I crossed out using Citi ThankYou points for paid American Airlines flights @ 1.6 cents each, and considered the other options:

Now, I was able to find a one-way there on the dates we needed (including a sweet set of flights landing within 15 minutes of ours!). And a one-way to get my little brother home. But not on the same airline. And American had nothing for award space (seriously, WTF, American?!).

That meant booking two one-way award flights.

I was so happy to share my points to include my little bro on the family trip!

I was so happy to share my points to include my little bro on the family trip!

I booked a one-way from Memphis to Honolulu on United, with a connection in Denver, for 17,500 Singapore miles.

And another one-way from Honolulu back to Memphis on Delta, with a connection in Minneapolis, for only 15,000 Flying Blue miles – that’s a fantastic deal!

Here’s how I did it.

Back with Delta

Citi ThankYou points transfer instantly to Flying Blue, which is awesome. So I booked the return flight first.

You can easily search for Delta flights on the Air France website. And you can travel from anywhere in Hawaii to anywhere in the continental US for only 15,000 Flying Blue miles each way.

I found several open flights within a couple of minutes

I found several open flights within a couple of minutes

I quickly found the flights I wanted, and clicked through to book ’em. But got an error message.

Noooo! Phantom award space? Site glitch?

Noooo! Phantom award space? Site glitch?

Then I called Air France at their New York office: 800-375-8723.

The agent quickly understood what I was trying to do. And explained Delta was pricing the award as two one-ways on their end because of the connection in MSP. He said it had been happening a lot lately and they are working to correct Delta’s busted-ass booking engine (yeah, good luck with that).

So if you hit the same snag, be sure to call. I gave the agent the flights I wanted, and gave him my card over the phone.

Within minutes, I got the itinerary, and saw my card had been charged $5.60.

The retail cost of the flight was ~$630 – which means each point was worth 4 cents apiece. Niiiice.

I advocate using points and miles because you won’t pay revenue prices.

There with United

At the same time, I transferred 18,000 Citi ThankYou points to Singapore Airlines. The transfer took less than a day. I transferred them on July 22nd in the morning. That same evening, they were in the account.

That was...

That was…!


The next morning, I verified the flights were still available by checking on – make sure you are NOT logged in when you search because United shows additional award flights for folks with elite status and/or the Chase United Explorer card.

Then, I called Singapore Airlines at 800-742-3333 to book. Again, within minutes, it was done.

I was charged in Singapore dollars, but it came out to $5.59 for the award. So be sure to use a card with no foreign transaction fees when you book these awards.

Another 4 cents per mile!

Another 4 cents per mile!

The benefit of booking this way

It’s quite easy to find award space for one or two on most routes – including to Hawaii.

Both Flying Blue and Singapore charge much less than Delta and United charge for their own flights.

With Flying Blue, you’ll pay 30,000 miles round-trip for coach seats on Delta – from any starting point in the continental US.

Delta charges 45,000 miles round-trip to Hawaii on their own planes.

And with Singapore, you’ll pay 35,000 miles round-trip for coach seats on United – from any starting point in North America. Or you can fly in Business for 60,000 miles round-trip (which is also a great deal if you want Business seats – I am fine with coach for flights 6 hours or under).

United charges 45,000 miles round-trip in coach and 80,000 miles round-trip in Business.

So the discounts are worth it, especially if you’re booking for more than one person.


Let's face it, I went to Hawaii for the Mai Thais

More money for Mai Thais! Another one, please and thank you 🙂

As a rule of thumb, if the seat you want costs over $600, it’s better to use 30,000 miles (or even 35,000 miles).

Because you’ll get at least 2 cents worth of value from each one. Otherwise, use your Citi ThankYou points to find a paid flight on American Airlines (where they’re worth 1.6 cents each through July 23rd, 2017). Or just pay and know you got a deal on cheap flights. 🙂

One other thing. If you want Flying Blue or Singapore miles, you’re in luck because they are both partners with all 4 transferable points programs: Amex Membership Rewards, Chase Ultimate Rewards, Citi ThankYou, and Starwood.

Bottom line

So that’s I ended up booking the trip. My little brother didn’t mind taking separate flights as long the arrival/departure times were similar – and they are.

The total cost was 32,500 Citi ThankYou points (realistically 33,000 because you have to transfer in increments of 1,000) and ~$11 for taxes. But that covered his entire trip to Honolulu and back – including the connecting flights.

Because Jay won’t be sharing a room with me any more, I’m glad to have my brother along for the ride – with no added room expenses.

In this case, it was worth it to book flights with Citi ThankYou points transferred to Flying Blue and Singapore instead of redeeming for American Airlines flights like my mom, stepdad, and I did.

I love reading about how peeps actually use their points and miles. So I thought it would be fun to post real-life bookings for a real-life trip.

Hope this got your travel gears turning – and feel free to add any tips on booking awards or things to do in Honolulu!

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About Harlan

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

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  1. This Hawaii booking series was a good real. I always forget about redeeming via partner airlines for domestic flights in the US. I always seem to remember doing it for flights overseas, but never at home for some reason.

    • Thank you so much, Ken! That’s so kind, I truly appreciate it and glad you enjoyed reading. 🙂

      And yes, there are some great deals to be had right here at home with international loyalty programs!

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