Award Trip Breakdown: First Class Flights to Alaska for $5

Andrea and I just got back from an Alaskan cruise (which I highly recommend) and in order to get to Alaska to meet the cruise, we had to book flights to Anchorage from New York. This post goes over exactly how we booked first class flights to Anchorage for $5.

When looking for flights to Alaska from New York during the summer, we quickly came across one realization: Flights are really freaking expensive! It was over $300 one way and it was difficult to find itineraries that were under $300 and did not involve really long layovers. I quickly realized I needed to use miles to get the best flights.

If you read other points and miles bloggers (and you should), they generally do not recommend redeeming miles from the legacy carries (America, Delta, United, US Airways) for domestic coach travel (12,500 miles one way) and especially domestic flight class (25,000 miles each way). Domestic first class is just essentially a bigger seat, some free entertainment and a meal that ranges from disgusting to somewhat eligible but at a cost of double coach travel.

United Domestic First Class

United Domestic First Class

However, looking at our situation, I decided to look for first class awards for the following reasons:

  • Flying NY to Alaska is over 8 hours of actual flying. That’s longer than many flights to Europe from New York. Most airlines charge 30,000 miles in COACH for one way travel to Europe, so for 5,000 less miles on a longer flight I got a better seat, food, drinks and entertainment.
  • First Class flights were pricing near $800 for our date. This resulted in per mile value of 3.2 cents ($800/25,000*100). For a domestic redemption this is fantastic as a good redemption can range from 1.5 – 2 cents per mile.
  • Since I’m 6′ 3”, I prefer business class and up on any flight over 6 hours. This isn’t to say I couldn’t survive this flight in coach (I’ve done 11 hours in coach) but I do value a more comfortable experience for 8 hours.
  • I have over 3 million miles across currently and every day I hold miles, they lose value. I don’t gain anything for holding them but instead as shown by the recent devaluations made by the airlines, my miles tomorrow may not get me as far if the cost of a trip in miles is increased.

Searching for availability was quite easy for this trip and I found some availability with United connecting in San Francisco. This would enable us to actually have lie-flat seats on the JFK to SFO segment before flying SFO to ANC. However, due to a schedule change, delays and cancellations this isn’t what we actually flew. I will discuss what happened to our initial flights and the process to fix them in a followup post on this.

Summary of Flights:

Departing (booked): United Airlines JFK-SFO-ANC for a cost of 25,000 miles plus $5 in taxes per person for First Class.
Departing (actually flown): United Airlines EWR-ORD-ANC for a cost of 25,000 miles plus $5 in taxes per person for First Class.

Miles Used: Transferred 50,000 Ultimate Rewards from my Chase Sapphire account to United. These points were obtained by using my Chase Sapphire Preferred card.

In short, we traveled to Alaska in style in First Class to start our cruise for a cost of 25,000 miles plus $5 per person. Compared to economy flights with long layovers over $300 and First Class flights costing $800, I think we made the right choice.

What do you think?



2 thoughts on “Award Trip Breakdown: First Class Flights to Alaska for $5

  1. […] actually had this exact issue happen to me for our flight to Alaska last month. We were initially booked on a 12pm flight (using miles) on United leaving JFK that connected in […]


  2. […] noticed the later Chicago to Anchorage flight at 5:40pm had only 2 first class seats left (remember I booked a first class award to Alaska so I only wanted first class seats which made this tougher). However the only possible NY to Chicago […]


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