Hawaiian Holiday – Introduction

  • Introduction
  • Four Points Sheraton SFO
  • American Airlines First Class SFO-LAX-HNL
  • Plane Spotting at HNL, Hawaiian Airlines Premium Lounge, Hawaiian Airlines First Class HNL-OGG-HNL
  • Honua Kai Resort
  • Maui Photo Essay
  • Hyatt Place Waikiki
  • American Airlines First Class HNL-LAX-ORD

Hawaii is, hands down, one of my favorite destinations.  While some may argue that the experience has gotten too commercial, or that the islands have become much too expensive to be an affordable holiday destination, I’m more than happy to call shenanigans.  I’ve been fortunate enough to drop in on the Hawaiian isle twice a year for the past two years and have been able to do so economically and without being trapped at Disney-esque luaus or paying $300/night for a hotel room.  I’ll freely admit, doing so wasn’t exactly easy and required me to do a lot of leg work prior to traveling, but I’ve always managed to make the trip affordable and interesting.

My previous trips allowed me to spend some time exploring Oahu, Maui, and the Big Island.  I’d had my eye on dropping in on Kauai for quite some time, and I had been casually checking prices on tickets from Chicago (ORD) to Lihue, Kauai (LIH) for several months.  It seems that trip would have to wait though.

In the beginning of February my partner came stumbling in to the house, dark hair flaked with snow, and offered this little tidbit of information – “Hey! Two of my good friends are going to Hawaii and they want to know if we would go with them?  Their family owns some condos that we could stay at for free!”  Despite not standing in front of a mirror, I can guarantee you that my eyes grew wide like a child on Christmas morning and my head cocked to the side like a golden retriever near a tea kettle.  Considering the cost of lodging is the most likely barrier to enjoying some time in Hawaii, I was keen to figure out if joining his friends was a workable option for the two of us.

I started poking around looking for tickets to Hawaii and was displeased to find nothing that would get us to the airport nearest the condos, Kahului on Maui (OGG), for under $1000.  Since I won’t consider flying to Hawaii unless the cost is under $400, we had an issue.  Or at least I had an issue.  Since Zach doesn’t travel as often as I do, he has much more flexibility when it comes to purchasing airline tickets since he will only take one or two trips per year.  Considering I take between 20-30 flights per year, the majority of which are paid, I have considerably less flexibility when it comes to price.

The offer of free lodging was just too good to pass up though.  I decided to strike a compromise…..

The years of flying with American Airlines (AA) and its oneworld partners have been kind to me.  I have managed to amass a small fortune in frequent flier miles which I have used to visit places such as London, Colombo, and Sydney essentially for free.  Despite cashing in my miles for a few wonderful trips, I still had quite a stockpile gathering dust in my account.  With the financial instability being reported at AA and keeping in line with the frequent flier mantra that miles always lose value over time and almost never gain value, I decided that it was high time that I cashed in the majority of my miles.

My favorite way to cash in AAdvantage miles is to redeem them for a oneworld explorer award.  These awards differ a bit from traditional point-to-point awards where you’d exchange a set number of miles to fly from your hometown to a single destination (Paris! Bali! Cairo!) and back.  The oneworld explorer awards are based on the amount of distance you travel.  So instead of flying to one location and returning home you are allowed to fly to multiple locations across the globe for a set number of miles depending on how far you travel.  The award rules can be fairly intricate when you read the fine print, and I don’t intent to give a primer on booking these types of awards (just yet).  Suffice to say that I was able to exchange a hefty portion of my miles (220K) in exchange for the following First and Business class ticket:

For those who prefer words over pictures, the ticket would fly me from San Francisco to Honolulu through Los Angeles before returning me home to Chicago for a short hiatus from travel all on AA’s domestic first class.  I would then pick my travel itinerary up again and head to Kuala Lumpur through Hong Kong before heading to Boston on Cathay Pacific (CX) and AA.  A few months after that trip I would again pick up my ticket and fly from Boston to Tokyo on Japan Airlines’ (JL) new Boeing 787 before connecting to another JL flight to Frankfurt.  To get home I’d take two flights on the newest member of the oneworld alliance, AirBerlin (AB), from Frankfurt to Berlin and on to New York City.  Again, after a small hiatus from traveling, I’d pick up the ticket for the final leg on Royal Jordanian (RJ) to Amman.

220,000 AAdvantage miles to visit Hawaii, Southeast Asia, Japan, Germany, and the Middle East all in First and Business class and $155 USD in taxes.  Now if that isn’t an amazing deal, I don’t know what is.

So at this point I had secured First class tickets (and then some, but we’ll talk about those other legs in separate trip reports) into Hawaii during the timeframe Zach’s friends were looking to visit, and clearly the lodgings were settled.  I simply needed to find a way to get from Chicago to San Francisco to start the trip and a way to get from Honolulu to Maui.

A quick search of AA.com turned up reasonably priced one way tickets from ORD-SFO at about $130.  I quickly booked a seat on an early morning flight to buffer myself against any cancellations or weather delays since ORD and SFO are both notoriously bad airports with regards to weather.  I then went about securing roundtrip tickets between HNL and OGG.  While there are a few options travelers can look at when trying to fly inter-island in Hawaii, there is no missing the fact that Hawaiian Airlines (HA) has come to absolutely dominate this market.  In the end, I booked the short hops with HA and the travel portion of our trip to Maui was settled.

The only bit of unfinished business I had was related to lodgings during the trip.  While the majority of my time would be spent free of charge in a condo owned by Zach’s friends’ parents, the convoluted routing that was created from buying a ticket ORD-SFO, booking a oneworld explorer award, and connecting on a separate ticket with HA meant that I needed to secure two nights of hotel on my own dime during this trip: an overnight in San Francisco prior to heading to Maui and an overnight in Honolulu prior to heading back to Chicago.

For my layover in San Francisco, I was able to find a relatively low rate at the Four Points Sheraton property.  TripAdvisor reviews for the hotel were rather mixed, but for less than $100/night it looked like a reliable option from a name brand I recognized.  I was also recently awarded elite status with the Starwood hotel group, which includes the Four Points brand.  This meant some small benefits, like free wi-fi, would lower the overall cost when compared to other properties in the area.

That left just the layover in Honolulu.  Hotel shopping in Honolulu can always be a bit difficult.  Even using a bidding website like Priceline or mystery purchasing through Hotwire can be relatively expensive depending on the time of year or day of the week you need lodging.  I tried to work my magic on Priceline with the help of BetterBidding.com, yet was unable to find anything.  Despite a gallant effort, Hotwire also failed me.  It was looking like I’d fail to find a low-cost option in Honolulu for the first time in two years when I noticed that the Hyatt Place in Waikiki was offering a 50% discount for a few days if you pre-payed your rate.  Knowing that my travel plans were solid and there was little room for changes between the four of us, I took the plunge and pre-paid the rate.

With that payment made, my travel planning effort for our Hawaiian Holiday was complete and I only had to sit back, relax, and count the days till my toes were in the sand and the sun was on my face.

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5 thoughts on “Hawaiian Holiday – Introduction

  1. We just returned from Maui as well and rented a condo via AirBNB in Kihei. It wasn’t the swankiest of places, but was quiet, clean and akin to having our own small apartment (at 110/night).

    We had a full kitchen so a quick stop by whole foods on the way to Kihei helped on food costs as we only ate out for dinner. As you said David, there are ways to keep costs in line in even the most expensive of destinations.

    • I’ll be doing a full report on the condos we stayed at, but it was actually a bit of a surprise when we arrived because it was nothing like what I thought it would be.

      Destinations are what you make it, and you can do almost anything for less than what it might seem at first.

  2. Pingback: Hawaiian Holiday – Four Points Sheraton SFO « ORD to Anywhere

  3. Pingback: Hawaiian Airlines Intra-island First (HNL-OGG-HNL) and HNL/OGG Premier Club « ORD to Anywhere

  4. Pingback: Hawaiian Holiday – Honua Kai Resort « ORD to Anywhere

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