How To Save $1,800 with United Airlines To Hawaii

This post is to walk you through how I managed to save a whopping $1,800 on flights repositioning from San Francisco to Honolulu for our winter break 2024.

When I decided to plan our spur-of-the-moment family trip to Asia this winter, we didn’t have a ton of flight options, except for one glaring choice: a route through Honolulu, courtesy of Hawaiian Airlines. Fun, right? Well, sure - if you can avoid spending your entire vacation budget just to get there. But don’t worry, I’ve got a few tricks up my sleeve to make it happen without draining our wallet.

Option 1: Turkish Airlines’ Award Redemption (The Holy Grail Of Deals)

The ultimate sweet spot is booking through Turkish Airlines - just 10,000 miles to get from anywhere in the U.S. to Hawaii. But here’s the catch: award availability disappears faster than free donuts at the office. Even though I heard there were plenty available, by the time I got around to it, poof, they were gone.

Option 2: Cash Tickets (A Heart-Stopping Reality Check)

Next up, cash tickets. Hawaii is on everyone’s bucket list, so prices are all over the place. Economy class tickets might run you around $250, which isn’t awful. But if you’re eyeing a lie-flat business class seat, prepare to shell out close to $2,000. For our family of four, even though $250 each person didn't sound crazy, that was still a minimum of $1,000 out of pocket - ouch.

Now, blowing a grand just to get to Honolulu wasn’t part of my game plan. So, my mission became clear: minimize that out-of-pocket cost as much as possible. This post is to walk you through how I managed to save a whopping $1,800 on flights repositioning from San Francisco to Honolulu -- and a bird's-eye view always helps. I took a step back and looked at which airlines fly from San Francisco to Honolulu. Here’s the breakdown - three airlines cover this route: Alaska Airlines, Hawaiian Airlines, United Airlines.

• Alaska Airlines: Great Perks, But Nope

Alaska Airlines was my top pick since I could really maximize my Citi AAdvantage Executive credit card. It gives us lounge access to both the American Airlines Admirals Club and the Alaska Airlines Lounge, let alone it helped me to earn two transpacific business class tickets between U.S. and Japan. As the primary cardholder, I can bring my immediate family members (spouse or domestic partner and children under eighteen (18) years of age) or up to two (2) guests traveling with me. The problem? The ticket prices of Alaska Airlines were sky-high. Both miles and cash rates were out of control, so I had to let it go.

• Hawaiian Airlines: So Much Aloha, So Little Savings

Next, I thought Hawaiian Airlines would save the day. They’re always hyped as one of the friendliest, most "Aloha spirit" airlines in the U.S. Honestly, I kicked myself for not keeping their Barclays co-branded credit cards both Hawaiian Airlines World Elite Mastercard and Hawaiian Airlines Business Mastercard, especially with the Alaska Airlines merger on the horizon. But sadly, no miles or special deals came to my rescue, so Hawaiian Airlines got the boot too.

• United Airlines: Ding, Ding, Ding - The Winning Ticket!

Finally, I turned to United Airlines. This is where things started to turn around, thanks to their United Airlines TravelBank.

Option 3: United Airlines TravelBank (The Secret Sauce)

If you don’t know about United Airlines TravelBank, it’s essentially an electronic piggy bank tied to your United Airlines MileagePlus account. You can stash money in there and use it like a gift card for flights. There are a few easy ways to fill up the United Airlines TravelBank and make your flights much more affordable.

• Chase IHG One Rewards Credit Cards

I earn United Airlines TravelBank credits through my Chase IHG One Rewards Premier Business credit card. One of the perks with the Chase IHG One Rewards Premier and Chase IHG One Rewards Business cards is up to $50 in TravelBank Cash each year - $25 in January and another $25 in July. You just need to sign up at IHG / United MileagePlus website, link your United Airlines MileagePlus number, and plan ahead because it usually takes two weeks to activate.

• Credit Card Travel Credits

You can use credit card travel credits to load up your United Airlines TravelBank. Since TravelBank purchases often code as travel expenses, you can use credits like the $300 from the Chase Sapphire Reserve credit card or incidental credits from cards like the Chase The Ritz-Carlton credit card.

• The "Amex Workaround"

For years, I have also been able to load my United Airlines TravelBank using the American Express (Amex) airline incidental credit (as of September 2024, this still works). Just make sure you’ve chosen United Airlines as your preferred airline. While this method isn’t guaranteed to work forever, it’s been solid so far. Officially, the fee credit applies to things like checked bags and in-flight refreshments. But the United Airlines TravelBank deposits of up to $50 or $100 is the easiest way to essentially turn those credits into cash. Keep this in mind: if you add funds to your TravelBank and it doesn’t trigger the credit, don’t call Amex. The purchase technically isn’t meant to qualify, so reaching out to them won’t help. The terms are pretty clear on what doesn’t count. Finger crossed!

How I Saved $1,800 with United Airlines TravelBank 

While booking our tickets on United Airlines.com, I chose TravelBank as the payment method. Aside from covering any remaining balance with my Chase The Ritz-Carlton credit card that had solid travel insurance, I managed to cover nearly $1,800 of our ticket costs to Honolulu using TravelBank credits. That’s right - zero dollars out of pocket!

• Bonus Tip: Booking Through United Airlines' Text Message Service

Here’s a cool trick I stumbled upon: United Airlines now offer text message support for booking tickets. When I hit a payment issue online with TravelBank, I switched over to text messaging. It was surprisingly smooth and only took about 15-20 minutes. All I had to provide was:

• Travel dates
• Flight numbers
• Routes
• Number of passengers
• Names of passengers
• United Airlines MileagePlus number

Extra Savings Option: Amex Business Platinum 35% Points Rebate

On top of all that, if you’ve got the Amex Business Platinum card, you can score a 35% points rebate on flight tickets. Remember this: pay with points first. While I didn’t snag a first-class round-trip deal this time, I still spotted using the 35% rebate to bring the ticket cost down from $650 to $450 (45,000 points) for Alaska Airlines one-way first class ticket. Since it’s a revenue ticket, you’ll also earn award miles, cutting the actual cost even further.

Final Thoughts:

This impulsive winter trip wasn’t planned far in advance, and my goal was simple: minimize our out-of-pocket expenses. There are plenty of ways to do that - from miles and points to United Airlines TravelBank credits and points rebates. The key is finding what works best for your travel style. In the end, I managed to save almost $2,000 on this leg of our journey. Was it worth the effort? Absolutely. Not only did we save a ton of money, but we also created some priceless memories for our family of four in our first-kid-as-a-college-freshman chapter!

What about your spontaneous family trips? I'd love to hear about your experiences and all the stories that come with them!