I’m up. I can’t sleep. A mix of anxious worry that I’ve forgotten something and gitty excitement. Oh, and happy birthday to me. My 36th birthday is about to begin, and there’s much to be excited about. The to-do list is racing through my head:
- Pick up my malaria prescription
- Buy micro SD cards for drone/go pros (I found out around 11pm the night before my card was corrupted and upon further research discovered a faster SD card would be better suited)
- Transfer a few Dave Matthews Band, John Mayer, and Howie Day shows to my phone
- Pick up rental car
- Buy a suitcase
- Oh ya, and pack
I pull myself out of bed at about 6:00am to start the tasks, methodically checking things off the to-do list I made the night before. To be fair, I’ve been planning this day, and the following 11 days for the past nine months, so I’m pretty sure I have everything down – from the minute by minute plans, to the Canadian flag patches we might have to sew onto our backpacks in case our Uniter-in-Chief decides to bomb someone while we are a bit closer to the Korean Peninsula.
I grab a quick workout and at 11:45am pull out of the driveway with NSPwife, NSPpeanut and NSPbabysitter. We rented a car for the hour drive, picking it up at a Hertz two miles from our house and dropping it off at O’Hare, just a few minute shuttle drive to International Terminal 5. We rented the car knowing that Uber is roughly the same cost, wanted to make sure the luggage would fit (needing an SUV), and to make sure we would be on our own schedule. The four of us are about to head around the world. While NSPwife and I have been to the other side of the world a couple of times, we’ve never truly traveled around the world. That’s about to change.
The first leg is Chicago to Hong Kong on one of my favorite flights: Cathay 807, First Class. I didn’t necessarily book this flight due to it being my birthday, but one First Class and Three Business Class seats aren’t necessarily easy to come by – and it happened to be one of only three dates to choose from with that award availability and seemed to work from a work schedule perspective. Luckily, a second First Class seat opened up about 10 days before the flight, so NSPwife and I will both be sitting up front.
After an 8:20pm arrival in Hong Kong and a quick planned jaunt into Kowloon, we will be staying at the Marriott Skycity hotel next to the Hong Kong airport, and take an 8:45am flight to Kuala Lumpur. NSPwife and I will be sitting in Business while NSPpeanut and NSPbabysitter have economy. This will be our first time there, a city that has long been on my bucket list, and I’m excited to try as much food as possible. It’s a quick 2.5 days in Kuala Lumpur, staying at the Grand Hyatt.
Then it’s on to Phuket, Thailand, one of NSPwife and my happy places. We are staying at the Hilton Arcadia, and while a bit dated, we love the location. Karon beach is a little less party-central, which is nice for NSPpeanut. It’s also a few minute walk to a number of local restaurants, shops, tailors, and massage places. I can’t wait to stock up on custom suits, get multiple massages, authentic Thai food, and lay by the pool and beach. We are risking it a bit by traveling at the start of the rainy season – but hoping the occasional scattered thunderstorm is all we have to deal with.
After Phuket, we make our way to Siem Reap by way of Bangkok on Bangkok Airways. I chose Bangkok Airways for two reasons: first, the times were excellent with an early morning flight and arrival into Siem Reap, and second, they don’t charge checked bag fees which would definitely add up after accumulating some extra baggage at the custom tailors and shops 😊. We will be staying at the Park Hyatt for our two days there and then make our way back to Bangkok. We arrive in Bangkok around 11:00am and booked the Grand Hyatt for the “day.” We’ll explore the city again for the day and hopefully grab a nap.
At 2:00am we work our way back around the globe, Bangkok to Abu Dhabi, with a five hour layover, and onto Washington Dulles. It may be a painful trek, but I’m hoping we sleep the entire way to Abu Dhabi, in Etihad Business Class. I’m hoping there is enough time in Abu Dhabi for a quick trip to Emirates Palace for breakfast, and then we head back to the States, NSPwife and I in First Class and NSPpeanut and NSPbabysitter in Business Class.
11 days, 21,391miles. It’s another whirlwind trip, but I learned from our last one that a relaxing beach destination in the middle is extremely rejuvenating, and added a fourth night (instead of only three) to the middle of the trip.

Our Travel Map, courtesy of gcmap.com
As you might surmise, the vast majority of this trip utilized miles and points. A quick breakdown is below:
Flights
- ORD to HKG: 70K Alaska Airlines for First Class and 50K for Business Class, totaling 240K miles. Taxes & Fees totaled $22
- HKG to KUL: 20K British Airways miles Business Class and paid economy tickets, totaling 40K miles. Taxes & Fees totaled $518
- KUL to HKT: 23,676 Citi Thank You Points. Taxes & Fees totaled $11
- HKT to BKK to REP to BKK: $943 for four seats inclusive of taxes and fees
- BKK to AUH: 40K American Airlines Miles and 197,088 Etihad Guest Miles. Taxes & Fees totaled $554
- AUH to IAD: 298,500 American Airlines Miles and 120,121 Etihad Guest Miles. Taxes & Fees totaled $326
- IAD to MDW: 26,487 Southwest Miles transferred from Ultimate Rewards. Taxes & Fees totaled $22
- Total miles used: 985,872
- Total cash paid: $2,397
In addition, we utilized $200 Travel Credits on both our Barclay Arrival and Bank of America Travel Reward cards, bringing the total to $1,997.
Hotels
- Marriott Skycity, Hong Kong: 1 night, 2 rooms, 31,815 Citi Thank You Points
- Grand Hyatt, Kuala Lumpur: 2 nights, 2 rooms, 2 Annual Certificates from the Hyatt Credit Card ($75 annual fee) + 15K points per night, totaling $150 and 30K points
- Hilton Arcadia, Phuket: 4 nights, 2 rooms, 19K points per night totaling 152K points
- Park Hyatt, Siem Reap: 2 nights, 2 rooms, 15K points per night totaling 60K points
- Total points used: 273,815
- Total cash paid: $150
There are a few things to mention about our itinerary. First, there are probably multiple ways we could have worked our way around the world with much fewer miles; however, after misconnecting with Matthew from Live & Let’s Fly a few times, I decided to just pull the trigger and book this itinerary. Business Class and First Class seats tend to go quickly, and since I booked the Cathay Flights, we were relatively locked in unless we wanted to delay our trip (which we didn’t). NSPwife’s reselling business also helps generate nearly 100,000 miles/points a month, so coupled with my past extreme credit card churning, we were, and are, flush with points, and setting up an itinerary to the desired schedule was more important than saving miles.
NSPwife is also a Hyatt Globalist member, and status matched to Hilton Diamond. So hoping there’s an upgrade or two along the way. And of course free breakfast at every stop at each hotel due to status and the ability to crash airport lounges with NSPwife’s Priority Pass membership that came with her American Express Ameriprise Platinum Card (no annual fee for year one).
Second, I really blew it with the HKT > REP > BKK flights. I kept waiting, and waiting, and waiting to make the reservation. I had assumed I was going to jump on an AirAsia or other ultra-low-cost carrier, and since tickets were just $45ish dollars, didn’t have a burning desire to book. Instead, about 45 days out when I tried to book, those flights doubled in cost, and with baggage fees were actually quite expensive. In hindsight, I should have transferred miles to Asia Miles and used Cathay Pacific to book on Bangkok Airways on a multi-city ticket. That would have been 15K miles per person, rather than the $250 per person (or 50% of our total cash outlay!!). Oh well. The one bummer was that when trying to book the flights with the Chase Portal to save 25%, they were pricing out the tickets at $757! Even the supervisors couldn’t manually ticket the flights, which was surprising, and frustrating. I mean, nearly a 300% price increase to book through Chase, that’s just insane, and frankly, disappointing that Chase would try to tack on that type of increase.
To put the value of these miles and points in perspective using just a microcosm of the travels, here is the cost of a single First Class Cathay flight alone:

Cathay First Class Ticket – Cash Value
So, yes, it’s 5:00am and there’s a bit to be excited about.
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