How to Get to Hawaii or Anywhere Else for a Destination Wedding Free or Cheap

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If you live in a western city with a direct American Airlines or Alaska Airlines post, skip this post and read All the 12,500 Avios Routes to Hawaii instead of this post. Currently that’s Los Angeles, Phoenix, Anchorage, Bellingham, Seattle, Portland, Oakland, San Jose, and San Diego.

Destination weddings don’t need to break the bank for attendees. Airfare can cost as little as the roundtrip aviation taxes to your destination ($11 to Hawaii), and, worst case scenario, you can always get $460 off the cheapest fare to your destination.

Lanikai MidPac Country Club
Lanikai and the Mokulua Islands from MidPac Country Club

There is a simple three-step process I would use to minimize the cost of airfare to a destination wedding in Hawaii:

1. Search on united.com for award space from your home airport to Honolulu.

2a. If there is award space you want, open the Chase Sapphire Reserve. Meet its minimum spending requirement to unlock its bonus. Book the space you found on united.com.
2b. If there is not award space you want, open the Arrival Plus.

3. If you open the Arrival Plus, set a Kayak Price Alert and purchase the ticket with your Arrival miles when the cash price dips.

For other destination weddings:

  1. Fill out a free credit card consultation form, and I will tell you what card(s) to open for the destination, time of year, and cabin of service you want.
  2. Meet the minimum spending requirements on those credit cards, and redeem your miles for the flights.

Let me go over these simple steps in detail at a beginners’ level, so anyone can follow along. No excuses for not showing up in Honolulu!

Step 1. Search for Award Space on United.com

Ideally you could use 35,000 miles and about $11 for a roundtrip from anywhere in the United States to Honolulu.

I say “ideally” because United will need to release award space at the Saver level for your award to cost 35,000 miles. Saver award space is capacity controlled, and airlines only release it when they expect there to be empty seats on the plane.

The low season in Hawaii is basically everything except summer, so if the wedding is in, say, February, your chances of finding Saver award space are great.

To search for Saver award space from your home airport to Honolulu, go to united.com. The search box is right on the home page. (Do NOT sign into united.com before searching for reasons beyond the scope of this post.)

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Enter your home airport as the starting point and Honolulu (HNL) as the destination. Select your preferred dates, the number of passengers, and “Search for award travel.” Click “Search.”

On the results page, you’re looking for an itinerary in the “Economy (lowest)” column that says “22.5k miles” and “Saver Award” like these three.

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Itineraries that say “45k miles” are useless to you.

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You’re looking for a desirable itinerary in each direction with Saver award space. Click through to the pricing page and it will say 45,000 United miles + $11.20 per person. All searches in this post were for two people, so my pricing page said double that: 90,000 miles and $22.40 for two people…

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…for this roundtrip from Columbia, South Carolina to Honolulu.

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If you’ve gotten this far, you are in good shape and will proceed to step 2a, getting a Sapphire Reserve. If no desirable itineraries appear with Saver space, proceed to step 2b, getting an Arrival Plus.

I think most people will find a desirable Saver itinerary outside of the summer months. United has tons of daily flights from San Francisco, Los Angeles, Houston, Chicago, Denver, and Newark to Hawaii with connections to everywhere else in the country. If you’re starting in a big United city like Chicago, there is Saver award space most days during the winter for two passengers.

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Even if you start in a small city like Columbia, South Carolina there is plenty of award space if you are flexible with departure and arrival dates by a day or two.

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First Class

You can easily fly First Class with miles instead of economy. This will cost less than double the miles. Unfortunately First Class to Hawaii is often just standard domestic First Class, which is hardly luxurious, though sometimes you get “Hawaii-configured” planes with a little more leg room or true flat-bed First Class.

The process to book First Class is the same as above except you need to find Saver award space in the “First Saver Award column.” Any itinerary listed as “40k miles” there is good. Beware, though, of “Mixed cabin” warnings. By clicking the warning, you can see which segment is in economy and which is in First class. You can book these Mixed cabin awards for the full First Class price.

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You can book one way in economy and one way in First Class for 62,500 United miles per person.

Step 2: Get the Right Credit Card

2a. If there was good space on United.com, get the Chase Sapphire Reserve.

If you found space in the previous section get the Chase Sapphire Reserve. It’s the best rewards credit card ever.

The Chase Sapphire Reserve comes with 100,000 bonus points after spending $4,000 on the card in the first three months.

The card earns 3 points per dollar on travel and dining expenses and 1 point per dollar on everything else.

After spending that $4,000 in the first three months, you will end up with at least 104,000 Ultimate Rewards–more if some of that $4,000 was spent on travel or dining. That’s enough for two roundtrips to Hawaii with one way in First Class and one in economy or 1,000 points short of three roundtrips to Hawaii in economy.

Ultimate Rewards transfer 1:1 instantly to miles with several airlines including United and Singapore miles.

Once all your Ultimate Rewards post to your Chase Sapphire Reserve account–which will happen when your first statement closes after you meet the minimum spending requirement–you’ll want to go back to united.com and make sure award space still exists on your dates. If it does, you could transfer 45,000 points per person to United miles and book the award. That’s instant and easy and dumb.

Instead, transfer 35,000 points per person for economy, 60,000 points per person for First Class, or 47,500 points per person for one way in economy and one way in First Class to Singapore miles. Singapore miles can book all the same Saver United award space you found, but for fewer miles. Look, I’m sure at this point your head is spinning, and this all sounds complicated, but this is easy as pie. Just read this post for the step-by-step process to do this all in 15 minutes.

If instead, when you go to united.com after getting your points, Saver space has disappeared–and airline award space is dynamic–all is not lost. The Ultimate Rewards from the Sapphire Reserve can be used for 1.5 cents toward the cost of any flight. In this case, skip to step three.

One final note on the Chase Sapphire Reserve: The card has a $450 annual fee due immediately. But in addition to the 100,000 bonus points, you get a $300 travel credit each calendar year: the first $300 in “travel” expenses you put on the card between now and December get refunded and the first $300 in “travel” expenses you put on the card after January 2017. That’s $600 you can use toward hotels, Airbnb, other flights, taxis, parking, car rentals, cruises, Uber, etc., etc. for the first $450 annual fee. That means you make $150 ($600 – $450 = $150) in the first 12 months you have the card. And you get the 100,000 bonus points. And you get free airport lounge access with the card. You can cancel the card any time in the next 12 months to avoid another $450 annual fee.

2b. If there was NO Saver space on United.com, get the Arrival Plus.

If your search in Step 1 turned up empty, get the Barclaycard Arrival Plus with 40,000 bonus miles after spending $3,000 in the first 90 days.

This card earns 2 Arrival miles per dollar on all purchases.

These are not true airline miles. They are just bank points–like those ones that Capital One is always advertising–that can be used to book any flight on any airline like cash.

The miles are worth 1 cent per mile toward any airfare you find.

After meeting the minimum spending requirement, you’d have 46,000 Arrival miles, which are worth $460 in free travel.

One cool thing about Arrival miles is how they are redeemed. You put any travel expense on the credit card including airfare, hotels, car rentals, and much more, and then you have 120 days to go online and redeem Arrival miles for a full or partial credit to offset that travel expense. (Redeeming is super easy. Here’s how.)

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That means if you get this card, you can immediately look to purchase your ticket to Honolulu with the card. Then whenever your bonus miles post, you can go in and use your 46,000 miles for $460 off the cost of your flight.

One final note on the Arrival Plus: the card has no annual fee for the first 12 months, then it is $89 per year. You can cancel the card any time before that annual fee to avoid it. Before canceling make sure to redeem any points, or you will lose them.

Step 3: Set a Kayak Price Alert to Stretch Your Arrival Miles Farther

When using Arrival miles, your miles go farther if you find the cheapest possible cash ticket.

(The same thing applies if you got the Sapphire Reserve, but United award space disappeared, so now you are here looking to use your points to book paid flights at a rate of 1.5 cents per point.)

The way I consistently get the best deals on paid tickets is to set Kayak price alerts.

Basically you set up an alert for a certain route on certain dates with a few clicks, then you get an email every morning with the price of those flights. When the price dips, you buy!

Go to kayak.com, and perform a search for your cities and dates. I like to start with a multi-city search when I am flexible to see how day of the week affects price. To perform a multi-city search, select “Show flexible dates” and “+/- 3 days,” and then select your flexibility from the dropdown.

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Results of a flexible search look like this with a matrix of prices depending on departure and return dates.

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From that info, narrow down your desired dates to one or two dates in each direction. Go back to the home search screen.

Search each possible pair of departure and return dates one at a time.

In the top left corner of the search results, click the orange button that says “Create a price alert.”

Repeat for each possible pair of departure and return dates.

You will start to get emails every morning from Kayak with all your price alerts. At the top of the email, you’ll see your dates and any change in price from the previous day. This is an email I used to get when I had three price alerts set.

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Down below is a graph with how the price has behaved over time.

Screen Shot 2014-12-01 at 3.28.53 PMIn ten seconds per day, you’ll quickly see how the price of the flights is moving. You’ll be surprised how often the price moves. At some point, when the price dips, BUY!

There is no science to this, but for me, when to buy has always been obvious. One day I’ll see a multi-hundred dollar drop. Or it will be stable for so long that the trip is now only three weeks away, at which point I would expect the price to rise.

I would expect someone who monitored a price alert for several weeks or months to shave a few hundred dollars off the current price from their home airport to Hawaii.

If you have the Arrival Plus, you can purchase the flights through the cheapest website with your Arrival Plus at any point, even before you earn its sign up bonus. Then sign into your Arrival Plus account and redeem miles to offset all or part of the ticket price.

If you have the Sapphire Reserve and made it to this step, you need to sign into your Sapphire Reserve account when the price drops and enter the Ultimate Rewards Travel Portal to book your tickets through there.

Not Going to Hawaii?

Combine Steps 1 and 2 into this: Fill out a free credit card consultation form, and I will tell you what card(s) to open for the destination, time of year, and cabin of service you want.

That consultation will also include basic instructions on how to redeem the miles I suggest getting. If those aren’t enough, you can hire my Award Booking Service to book your ticket for $125 per person.

Recap for Hawaii

1. Search on united.com for award space from your home airport to Hawaii.

2a. If there is space you want, open the Chase Sapphire Reserve. Meet its minimum spending requirement to unlock its bonus. Book the space you found on united.com.
2b. If there is not space you want, open the Arrival Plus.

3. If you open the Arrival Plus, set a Kayak Price Alert and purchase the ticket with your Arrival miles when the cash price dips.

Questions? Leave them in the comments.


Editorial Disclaimer: The editorial content is not provided or commissioned by the credit card issuers. Opinions expressed here are author’s alone, not those of the credit card issuers, and have not been reviewed, approved or otherwise endorsed by the credit card issuers.

The comments section below is not provided or commissioned by the bank advertiser. Responses have not been reviewed, approved, or otherwise endorsed by the bank advertiser. It is not the bank advertiser’s responsibility to ensure all questions are answered.

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5 COMMENTS

  1. Sorry but this isn’t the best advice as there are cheaper ways to get to Hawaii on UR than singapore miles from the east coast. ex. 30k roundtrip transferring to flying blue

      • True but with flexible points like UR it makes sense to check availability first for the best options and then transfer points. Why waste points when you can do it cheaper elsewhere? It especially adds up if you are booking tickets for more than one person.

  2. I tried the 35K booking through Singapore and ran into something odd. Even ran the itinerary through two agents and got the same quote.

    Turns out I could book a 35K roundtrip IF both directions were non-stop. Initially I found a reasonable 1-stop layover in Houston on the return, and both agents priced the ticket as 25K + ~$200 because the system automatically interpreted it as a domestic roundtrip with a stopover in Honolulu.

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