The City Miler is the personal blog of David Slotnick, a points and miles-obsessed travel junkie, travel writer and native New Yorker. Follow for my latest travel (and travel "hacking") tips, tricks, reviews and photos.

$33K Flights for $168 — How I Booked My Honeymoon in First Class

$33K Flights for $168 — How I Booked My Honeymoon in First Class

This fall, I’m getting married and taking a nearly three-week honeymoon to Japan and Hawaii. When my fiancée Reni and I started talking about our honeymoon, one of our goals was to use points and miles to fly in business or first class for the longer legs.

While I love flying in premium cabins, I usually opt to fly in coach to save miles (or money) for the next trip. Our honeymoon, though, seemed like a good time to splurge. We wanted to celebrate the special trip with a fun travel experience, and we wanted to be well-rested so that we could have more energy to explore when we hit the ground.

Because we had been talking about getting married for a while before we got engaged, most of my points-collecting and spending strategy over the past two years has been centered around the honeymoon. Reni is less into the travel “hacking” thing than I am, but she took advantage of a few credit card offers and other points-and-miles opportunities as well.

First, a little about the coach vs. business/first class debate in travel "hacking"

Generally, there are two distinct types of points and miles buff: The first type of people want to travel more often, and they stick with flying coach in order to save miles for more trips. Usually, it seems they either focus all of their points on flying and pay cash for Air BnBs or hotels or, if using points for lodging, sticks with the lowest category (and priced) property possible.

The second type wants to travel more opulently, spending miles on first class flights with huge lie-flat seats and fully enclosed suites. They love using points to book extravagant hotel suites or waterfront cabanas at luxurious beachfront properties that they couldn’t otherwise afford, and are obsessed with finding the most expensive cash product for which to use the fewest amount of points, generating the highest possible cents-per-point (CPP) value.

Obviously, that's a broad and simplistic generalization. Many, including me, fall somewhere in the middle and list a bit towards one of those general types — in my case, the first type. For the most part, I want to travel as much as possible, and even though I hate redeyes and can’t really sleep in coach, I often find it hard to justify spending double the miles or more to fly in a more comfortable class of service, even with low cash prices these days for economy tickets.

But part of why I like this game is that it means you can do things you otherwise can't afford, such as traveling up front. Sometimes you might want to spend up if it’s a special occasion, or it’s a really long flight and you don’t want to spend it sitting with your knees crushed into the hard plastic in front of you (I’m looking at you, United), or you know you don’t have another use for the miles. That last scenario, for example, is what led me to fly business class to London this winter — my stock of American Airlines AAdvantage miles were earmarked for the trip, and since I was able to find a cheap flight home with Norwegian, I decided to treat myself for the outbound. In the case of our honeymoon, I think it’s safe to say that the “special occasion” category applies.

As an AvGeek, I’ve been so excited for the flights that Reni almost thinks I’m looking forward to getting to the honeymoon more than the trip it self!

Where to go?

When we got engaged, we started talking through honeymoon ideas. The most important thing to us was that the trip have two stops; we wanted to explore and have an adventure for most of our honeymoon, and end the trip with a few days relaxing by the beach. We looked into New Zealand or Australia combined with Tahiti or Bali, even though using miles would be tough from the U.S. Eventually we decided that New Zealand might more fun as a long trip a bit later on, so we crossed that off the list. 

We played with a few ideas and landed on Japan for the larger part of our trip. It’s been on both of our travel bucket lists for a long time, and it’s a super popular destination right now. For the relaxing beach part, we decided on Hawaii. It’s a great time of year on the Hawaiian islands, and it’s so easy to get there from Japan — Hawaii isn’t somewhere we’d normally go without another stop, making this a great chance to visit. We weren’t sure what island we wanted, so we planned to book a flight to Honolulu and figured we’d just catch a quick inter-island flight if we moved beyond Oahu.


Because we aren’t flying a direct roundtrip, we booked our flights one at a time. It’s usually more cost-effective to do that when booking award travel, anyway.

We booked the New York-Japan flight first, about ten months in advance. Because our stock of points was heavily with Chase, we decided to fly Korean Airlines, transiting through Seoul. We weighed a few other options, including booking JAL with Chase Ultimate Reward (UR) points transferred to British Airways Avios, or United Airlines or ANA with UR points transferred to United MileagePlus miles. However, Korean Air has a well-reviewed premium product, and has generous saver availability in first and business class for members of Korean Air Skypass. Also, we didn’t want to put a ton of effort into finding two premium seats or having to wait to book until last-minute when new saver seats on other airlines were made available, so Korean was the best choice for our needs.

Searching for award seats on Korean Air is easy. Just make sure to select "redeem miles" and log in. To search for multiple seats, you can use a tool like ExpertFlyer.

Sidenote: United has fairly decent saver availability in premium cabins on its own metal and, preferably, on ANA, either 11 months in advance or within a few weeks of travel. For this trip, though, we didn’t see anything that worked. 

Once we found two available premium cabin seats, we transferred Chase UR points to Skypass miles and booked. It’s worth noting that, in order to book an award ticket for someone else, Korean requires you to prove a familial relationship. As far as I know, this is the only airline with this kind of requirement. Since Reni and I aren’t married yet, we each just booked our own tickets on two separate reservations and chose seats next to each other.

The seat in Korean Air's A380 first class. Courtesy Flickr user TravelingOtter.

Although we would have been happy in business class, we decided to spend the extra 10,000 miles each for first class. We’ll be flying JFK-ICN on Korean Air’s A380-8 — my first flight on the double-decker Airbus — in first class on the lower level. Highlights include spacious and comfortable beds, three (!!!) on board bars accessible to first-class passengers — including this insane lounge — a cool (though unnecessary) duty free shopping display and, most excitingly, the option to have bibimbap for dinner on board! We only cared about a premium cabin for the longhaul flight, but the ticket included first-class travel on the ICN-NRT connection as well. That flight is on an A330-200 in the single row of first class.

Booked! Note: The ICN-NRT flight was originally on a 777, but was changed to an A330.

We booked the Japan-Hawaii flight next, before we planned our full Japan itinerary. We decided to book our departure out of Tokyo, figuring we could get to the airport easily enough from anywhere, even if we ended up in Kyoto or another city.

Note: Delta, Japan Airlines and Hawaiian Air each have one daily flight between Osaka, near Kyoto, and Honolulu.

Because we were flying from Tokyo, we decided, based on the points we had, that United was the most ideal option. It was still nine months out, so we found availability fairly easily. Because there was first class availability but not business class, we decided to splurge again. Plus, I’m excited to fly United’s legacy first class product (currently marketed as "Polaris First") before it disappears forever to make way for the new Polaris business class! We had a decent stock of United MileagePlus miles from flying, dining rewards and a handful of other random promotions, and supplemented them heavily with Chase UR points transferred over.

United's award chart between Japan and Hawaii

We settled on spending our time in Hawaii in Maui, so we booked a quick hop from Honolulu on Hawaiian Air paying cash — Hawaiian Air inter-island tickets are usually less than $100 each way booked in advance.

The flight home was actually the hardest one to book. Finding premium cabin award availability between Hawaii and the continental U.S is notoriously difficult, since it’s such a hot leisure destination and so many honeymooners have the same idea. We thought about just booking coach so we could fly straight from Honolulu to New York without jumping through availability hoops, but all of the direct flights were redeyes (ugh). I spent a while searching around and managed to find two saver-level seats (or what seems to be saver based on Delta’s nonexistent award chart) in Delta One from Los Angeles to New York-JFK, so we decided that instead of flying the direct redeye, we’d book the LAX-JFK flight on Delta One, fly in coach on Delta from Maui to L.A. (using Delta SkyMiles for both flights) and spend an overnight in L.A.

It can be tricky to find saver availability (40,000 SkyMiles) for Delta One transcontinental.

A litte while after we booked, Delta came up with other plans, implementing a schedule change and moving our OGG-LAX flight up about thirteen hours. That meant we’d lose our last night in Maui and have to fly a redeye to Los Angeles a day early. First of all, we wanted to enjoy the last night of our honeymoon, and second, if we’re going to fly a terrible redeye, we might as well get a nonstop!

Delta One on a Boeing 767 (the same type of plane operating our flight). Photo courtesy of Delta.

I called Delta asking if the airline could either help us find another flight or offer anything to make up for the big schedule change. The phone agent helped move us to a flight to LAX at our original time, but departing from HNL instead of OGG. This worked for us because even though we’d have to get to Honolulu from Maui and we’d lose that morning, we’d at least get to keep the last night in Maui. I asked if they could offer any kind of compensation to cover the flight we now needed to book to Honolulu, or maybe an upgrade on that flight or some of our SkyMiles back, and the agent told me to contact corporate customer support. I did, and they laughed at me and said that schedule changes were my problem to work around.

I’ll be honest, I was annoyed! Sure, the original agent reaccomodated us (out of a different airport), but a half-day schedule change seems beyond what's normally acceptable. I figured that it couldn’t hurt to complain on Twitter, so I did, mentioning @Delta. Within minutes an agent asked me to send a direct message explaining the situation, and about ten minutes later he got back to me offering both Reni and I cash vouchers towards a future flight, and giving me instructions on how to request compensation for the OGG-HNL flight once we return. I’ve said it before and I’ll say it again, despite the weird phone customer service agent; Delta customer service is fantastic. Much better than United.


Here were our flight costs in points and actual money.

JFK-ICN-NRT (Korean Air, first class) 

  • Cost in points (each): 80,000 UR points (transferred to SkyPass) plus $33.66 in taxes and fuel surcharges.
  • Cost for the cash ticket: 10,645.65
  • Cents per point (CPP): 13.3 (factoring in the taxes and surcharges)

NRT-HNL (United Airlines, first class)

  • Cost in points (each): 62,500 United miles and UR points plus $38.96.
  • Cost if we’d paid cash: $4,589 ($984 if booked as part of a nonrefundable roundtrip)
  • CPP: 7.3 (1.5 if you consider the price of the flight as half of a roundtrip).

HNL-OGG (Hawaiian Airlines, coach)

  • Cash (under $100 one-way)

OGG-HNL (Hawaiian Airlines, coach)

  • Cash (under $100 one-way)

HNL-LAX (Delta Airlines, coach)

  • Cost in points (each): 22,500 Delta SkyMiles plus $5.60
  • Cost if we’d paid cash: $348.20 (basic economy is $25 cheaper)
  • CPP: 1.5

LAX-JFK (Delta Airlines, Delta One [business class])

  • Cost in points (each): 40,000 Delta Skymiles plus $5.60
  • Cost if we’d paid cash: $1,058.20
  • CPP: 2.6

So for each of us, that’s nearly $17,000 worth of flights for $83.82 and 205,000 miles. Or combined, more than $33,000 worth for $167.64 and 410,000 miles. Not too shabby!

How we got the points

410,000 miles is a lot, especially considering we accumulated them in less than two years. In addition to flights with Delta and United, credited to those respective frequent flier programs, and a handful of bonuses and regular earning through dining rewards and shopping portals, we earned most of the points through credit card signups and regular spending. I also earned around 50,000 Chase UR points through referrals to friends and Reni. Here are the cards we opened and used.


  • Chase Sapphire Preferred: 50,000 UR point signup bonus
  • Chase Freedom: 15,000 UR point signup bonus
  • Delta Gold SkyMiles Business Card by Amex: 60,000 SkyMile signup bonus
  • Delta Platinum SkyMiles Card by Amex: 70,000 SkyMile signup bonus


  • Chase Sapphire Preferred: 50,000 UR point signup bonus

For the sake of booking our honeymoon, that really isn't that many cards. We could have been more aggressive, but ended up not needing to be. We've both also opened Chase Sapphire Reserve cards and I've opened a few others, though miles from those cards weren't used to book our honeymoon.


Hotels, Food, Cars

It would have been really cool — and definitely manageable — to book most of our lodging for free with points, but we decided to pay cash for all of our hotels. 

I definitely like saving money on hotels, and I actively collect hotel loyalty points through stays, promotions and credit card offers. However, like the first type of travel "hacker" I focus more on flights, and am generally happy to couch surf or stay in a cheap hotel and Air BnB. The hotel points I collect are for trips when our budget otherwise couldn't handle a full-service hotel and we want to enjoy those accommodations.  

On our honeymoon, two things come into play. One, since it's a once-in-a-lifetime trip, we have some budget flexibility we normally wouldn't. Two, we wanted to stay in the most ideal locations and properties without thinking about points. I really love different hotels and hostels and the cool, unique vibes, history and experiences they have. Because of that I have a particular rule I follow: whenever practical and possible, don't turn down a hotel you'd otherwise choose because of points. We'll be staying in a mix of properties, including some we'll earn points on and some we wont, such as an independent ryokan.

We're renting a car in Maui and are also paying cash for that. Car rentals is an area of travel "hacking" in which I have very little experience. At the very least, we'll be maximizing return on the rental by taking advantage of certain car rental elite benefits provided by the Chase Sapphire Reserve, earning 3x points by using the card and using primary insurance provided as a benefit with that card.

As for food...well, even if you can get free travel with points and miles, food is always a cost to consider. Needless to say, we're beyond excited for some incredible meals and snacks in Japan.

Activities, including admission costs, tours, tickets etc. also aren't going to be covered by points. Again, this is what comes out of the cash budget you still need to have whenever you travel with flights and hotels covered by points. We may use flexible points currencies for our Japan rail passes, too.


One of the reasons I started this blog was to show that even if you don't fly a lot, and even if you don't want to open new credit cards every other week while carrying out manufactured spending, it's still possible to earn enough points to travel for cheap, even in first class. By opening five credit cards, taking advantage of low-hanging fruit in the form of easy programs and offers and by maximizing our everyday credit card spending, my fiancée and I have been able to book $33,000 worth of first class travel for around $168. If we can make this happen, so can you.

Just remember the big rules of the credit card rewards game. Pay off all your statements, in full and on time, to avoid interest charges and late fees. Never spend more on credit cards than you can afford to pay off. Don't spend money that you wouldn't have spent otherwise just to earn rewards points. Keep an eye on your credit score, and hold off of new applications if you're applying for a mortgage or other large loan.

As always, let me know if you have questions! Also, I'm grateful if you share any Japan or Maui tips in the comments. Finally, make sure to subscribe to new posts by entering your e-mail address below.

Happy travels!

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