Last month, I booked an award from Buenos Aires to Honolulu for 25,000 Singapore miles and about $100 in taxes. The booking illustrates a few topics:

Sweet spots and how to find them
Awards you should book speculatively
Booking awards with foreign programs

The Problem
I have to get to Hawaii for my brother's wedding in February. The main problem is that I don't know where I'll be in February to book the ticket to Hawaii.

This is the fourth post in a series about how I used Singapore miles to book United BusinessFirst between San Francisco and Buenos Aires, as well as a review of the product and travel experience. 

Trip Report Part I: United Clubs in San Francisco and Houston
Trip Report Part II: United BusinessFirst Houston to Buenos Aires
Anatomy of an Award: Booking United BusinessFirst with Singapore Miles
Changing a Singapore Award (future post)

In the last post of this series, I explained why and how I went about booking United Business Class with Singapore Krisflyer miles from the United States to

This is the third post in a series about how I used Singapore miles to book United BusinessFirst between San Francisco and Buenos Aires, as well as a review of the product and travel experience. 

Trip Report Part I: United Clubs in San Francisco and Houston
Trip Report Part II: United BusinessFirst Houston to Buenos Aires
Anatomy of an Award: Booking United BusinessFirst with Singapore Miles (this post)
Changing a Singapore Award (future post)

I had a one week window during which I wanted to fly Business Class from San Francisco, back home to Buenos Aires.
Checking Award Space of

Last week I booked myself an award from Chicago to Buenos Aires in United economy for 30,000 United miles + $5.60. This award was very simple, but it illustrated three interesting concepts:

When will last second award space open up?
United's secret extra award space.
The trick to save $75 on last second United award bookings.

Last Second Award Space
I had been searching award space for months from Chicago to Buenos Aires, and there was never any on the inflexible date I wanted to fly.

With the proliferation of transferable points like Chase Ultimate Rewards, American Express Membership Rewards, Citi ThankYou Points, and Starwood Preferred Guest Starpoints, Americans have access to cheap awards through tons of foreign programs.

Here are five underpriced awards on foreign award charts and how to get the miles needed to book the awards.
1. Singapore Awards Between Hawaii and the Americas
Singapore Airlines puts Hawaii and Central America--you know, those two places that are thousands of miles apart--into one region.

I just booked myself a $1,233 economy flight from Hawaii to Chicago for 17,500 Singapore miles and $5.

You probably already have the miles I used, so you're only a 10 minute phone call away from a trip to Hawaii that costs thousands of miles fewer than it "should."

The basic idea is that you don't want to use United, American Airlines, or Delta miles to fly to Hawaii. You want to use their planes, but you want to book those flights with miles issued by foreign airlines, which for whatever reason, offer far cheaper award prices to

Singapore Airlines is altering its routes to the United States in October 2016. Currently, Singapore flies from four American cities to Singapore with stops along the way in Europe and Asia.

San Francisco to Seoul (ICN) to Singapore
San Francisco to Hong Kong to Singapore
Los Angeles to Tokyo (NRT) to Singapore
Houston to Moscow (DME) to Singapore
New York (JFK) to Frankfurt to Singapore

Singapore is making several changes though.

Citi ThankYou Points are transferable to one hotel and 12 airline programs.

The Ink Plus currently offers:

60,000 bonus Ultimate Rewards after spending $5,000 in the first three months
5 Ultimate Rewards per dollar at office supply stores and on cellular phone, landline, internet, and cable TV services
2 Ultimate Rewards per dollar at gas stations and hotel accommodations
1 Ultimate Reward per dollar on all other purchases
$95 annual fee

That means you'd have at least 65,000 Ultimate Rewards after meeting the minimum spending requirement (60,000 for the bonus, and 5,000 for 1x spending), enough to fly several Korean and Singapore First Class routes with no

You can book yourself a tour around the Caribbean and South America stopping in three places for only 64,500 miles total with half the trip in a flat bed. By stopping in three places, I am referring to actual destinations, not connections that have to be under 24 hours.

This incredible deal relies on piecing together four sweet spots awards into one big trip.