No Award Seats? No Problem! How I Booked 5 Round-Trip Flights to Hawaii With Citi ThankYou Points (for Less Than What the Airline Charges)

INSIDER SECRET: When airfare is cheap, you’ll often spend fewer points booking a flight through a bank travel portal than if you redeemed airline miles for an award flight.

One of the best feelings in the miles and points hobby is snagging a hard-to-find award flight or hotel stay. And it’s even better when you wind up paying fewer points than expected.

I recently booked 5 round-trip tickets to Hawaii on United Airlines for my family and didn’t pay a cent – yes, all on the same plane! Using Citi ThankYou points from my Citi Premier℠ Card and Citi Prestige® Card, I was able to book these flights even though there were no award seats available for a group our size.

This is a perfect example of why collecting flexible points is the key to unlocking free travel. Even if you can’t find the award seats you want, redeeming Citi ThankYou, Chase Ultimate Rewards, or American Express points through the bank’s travel portal gives you the freedom to book just about any flight you want, without blackout dates.

I’ll show you how you can do the same thing if you’re stuck and can’t find award flights – and why you might actually save points booking this way.

We’re off to Hawaii with Citi ThankYou points (even though there were no award flights available) – and it’s not costing us a penny. (Photo by crisserbug/iStock by Getty Images)

When No Award Flights to Hawaii Were Available, Citi ThankYou Points Saved the Day

No Luck Finding Southwest, United Airlines, or Air Canada Award Flights

Hawaii is an incredibly popular destination and is on many of our bucket lists, so it’s understandable that award flights can be tricky to find, especially during peak travel periods like school breaks. I’d wanted to book a trip to Hawaii with my boyfriend and three kids right after school lets out for the summer, but wasn’t able to firm up our plans far in advance due to some uncertainties in our schedules.

And, I admit, I was a little disappointed when Southwest launched their Hawaii flights with few to no connections from East Coast cities (we live in Western New York). That was going to be my angle (especially since I earned the Southwest Companion Pass earlier this year and have a stash of Southwest points from cards like the Southwest Rapid Rewards® Priority Credit Card).

Folks on the East Coast haven’t gotten much aloha from Southwest’s new flights to Hawaii. (Photo courtesy of Southwest)

So I went with plan B, which was to book United Airlines flights to Hawaii using Singapore Airlines miles. That might sound strange if you’re new to miles and points, but there’s a good reason to NOT use United Airlines miles for flights to Hawaii from the mainland US or Canada. United charges 45,000 miles round-trip in coach for an award flight, but you can book the exact same flights with Singapore Airlines miles (they’re Star Alliance partners with United) for 35,000 miles instead.

Singapore Airlines miles are super easy to earn, too, because they’re a transfer partner of all the flexible points programs:

Singapore Airlines charges the same price for award flights on Air Canada (also a Star Alliance airline), and we have the option of flying out of Toronto, so that was another airline I searched. Unfortunately, when I looked for award flights on either United or Air Canada with all combinations of departure and arrival airports, there were no good options for five people on the same aircraft.

On to plan C…

Use Your Flexible Points to Book Cheap Flights Through a Portal Instead

This should have actually been my first line of attack, but I made the assumption that paid flights to Hawaii from any of our departure airport options (Rochester, Buffalo, Syracuse, and Toronto) would be crazy expensive. If your home airport is smaller and especially on the East Coast you’ll get my meaning – we don’t often get treated to super low fare sales to Hawaii like folks in major West Coast cities do.

When I couldn’t find award seats, I did a Google Flights search for our travel dates. The planets must have aligned the day I was searching because incredibly, there were flights available from Toronto to Maui on United Airlines (via Chicago) for just $427 round-trip on our exact travel dates. That’s very cheap for flights out of Toronto.

I’d originally planned to use Citi ThankYou points by transferring them to Singapore Airlines to book award flights, but instead I headed right over to the Citi ThankYou travel portal and did a search for the flights I found. When you have Citi ThankYou points from the Citi Premier, they’re worth 1.25 cents each towards travel (airfare, hotels, rental cars, and cruises) booked through the portal.

And – ta da! The flights I’d searched were on there, at the exact same price I found on Google Flights. At the 1.25 cents per point rate, each flight would cost 34,152 Citi ThankYou points. That’s less than I would have paid had I transferred points to Singapore Airlines to book United Airlines flights instead. The cash price of the flights for 5 of us would have been over $2,100. Score!

Still Can’t Believe It – I Found Paid Flights That Cost Fewer Citi ThankYou Points Than Transferring to Singapore Airlines for United Award Flights

Another bonus – because these are paid flights, we’ll earn airline miles for our trip. Also, the points price includes taxes (which can be a little hefty flying out of Canadian airports), whereas if I’d booked an award flight I’d be on the hook for the miles and additional taxes and fees.

It just goes to show that focusing on award flights shouldn’t be your only strategy. When airfare is cheap, you might yet get a better deal by redeeming your points through a bank travel portal instead. It’s always worth a look even if you think prices will be sky high.

After pulling the trigger on the flights, I booked 5 nights at the Grand Wailea with Hilton Honors points, which, if paid with cash, would cost nearly $4,200. And we’re spending another 3 nights at a Choice Hotels property which would cost nearly $1,100 – while not the best points value, it’s perfect for that time in our trip. We’re getting over $7,000 worth of family travel by redeeming miles and points.

Want to know more about using flexible points to book free travel? Check out these posts:

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