How I Booked 10 Business Class Flights for Less Than $1,000

Being savvy in how you earn and redeem your valuable miles/points for travel is equal parts art and science. I have been practicing these skills over the last 12 years of traveling for work and fun. In likely my best travel accomplishment to-date, I successfully booked 10 flights in business class for my upcoming trip to Asia for less than $1,000. Here’s how I did it, and what I learned along the way…

Flight 1, 2, 9, 10 (Round-trip Chicago to Hong Kong)

  • ORD - EWR - HKG - SFO - ORD

  • United First on the Boeing 757-300

  • United Polaris Business Class, Lie-Flat Seat on the Boeing 777-200 and 777-300ER

  • Total cost: $700 cash

Likely the most challenging flights to get a reasonable business class ticket are the trips across the pond. The lesson here is: book early. There are a few reasons why. First, long haul prices are usually set to their level-point 6-8 months ahead of time. Secondly, if you are planning to use Global Premier Upgrades (GPU’s), the likelihood of getting the upgrade confirmed at booking appears to be better when booking relatively far in advance. For this route, I booked a round-trip ticket from Chicago to Hong Kong for $1,100 in Economy. I used a $900 travel credit I had from a previous cancelled trip, so the net expense was just $200. Additionally, I paid my friend $500 for two of his United Global Premier Upgrades (GPU’s) to secure a confirmed upgrade to business class for both legs. Confirmed GPU’s (instead of being put on an upgrade waitlist) are nearly impossible to find these days. You must search diligently and book them if you find them (because they might be gone the next day).

Flight 3 (One-way Hong Kong to Singapore)

  • HKG - SIN

  • Singapore Airlines Lie-Flat Business Class on the Airbus A350-900

  • Total Cost: Free (30,500 Chase Ultimate Reward Points transferred to Singapore Airlines KrisFlyer Program)

The unrest occurring in Hong Kong these days is disturbing and sad. However, the impact on flights was interesting. Demand fell significantly, causing supply to increase, which lowered prices to the city. The lesson here is: do not avoid a city all together based on geopolitical reasons if it can get you to a region for a low cost, being a connection point to somewhere else. I initially planned on staying in Hong Kong longer, however given the circumstances I decided to use it as a connection point to Singapore. For this flight I leveraged the Chase Ultimate Rewards points transfer program to Singapore KrisFlyer. Singapore Airlines has some of the best award redemptions in the industry; a one-way business class ticket was 30,500 points, valued at $610 (based on 2 cent per mile valuation from TPG). The price to pay cash for this flight in business class was a whopping $1,290. Instead I got it for free.

Flight 4 (One-way Singapore to Ho Chi Minh City)

  • SIN - SGN

  • Singapore Airlines Lie-Flat Business Class on the Boeing 787-10 (Dreamliner)

  • Total Cost: Free (21,500 Chase Ultimate Reward Points transferred to Singapore Airlines KrisFlyer Program)

While I knew I wanted to visit Singapore on this trip, my next destination was relatively undecided. I explored all options within the region including Bali, Thailand, Philippines and Vietnam. I focused my research on the best flight redemptions, but also based on the destination itself. Many of my friends have spoken very highly of Vietnam based on their own travels, so it quickly rose to the top of my list. I, again, leveraged the Chase Ultimate Rewards points transfer program to Singapore KrisFlyer for this flight. The flight was 21,500 points to book, valued at $430. The price to pay cash for this flight was $690. The lesson here is: since the flight valuation (on points) is less than the paid fare, it is a good deal to use points. Plus this flight is on the Dreamliner…one of the best planes in the industry.

Flight 5, 6 (Round-trip Ho Chi Minh City to Phu Quoc)

  • SGN - PQC

  • Vietnam Airlines Recliner Business Class on the Airbus A321

  • Total Cost: $281 cash

I am a Marriott enthusiast, and I always try to stay updated on their new hotels. A few years ago I remember reading about a new hotel, the JW Marriott Phu Quoc Emerald Bay. I am usually somewhat wary of booking a BRAND NEW hotel, as there is usually an uptick time for the hotel to become fully operationalized and ready for guests. The good news is, this hotel has now been open over two years and the reviews are amazing! In fact, it was recently rated as the #6 hotel in the world by Travel & Leisure. I knew I could not miss this destination. For this flight I booked with cash directly on the Vietnam Airlines website for $281; as compared to using the Chase Portal where the price was $550. The lesson here is: always check the price directly on the airline website before booking!

Flight 7 (One-Way Ho Chi Minh City to Seoul)

  • SGN - ICN

  • Asiana Airlines Angled Lie-Flat Business Class on the Airbus A330

  • Total Cost: Free (46,193 Chase Ultimate Rewards Points direct booking)

South Korea is known for being an extremely technologically advanced country (right up my alley). Along with a bustling nightlife and amazing food, I knew I had to try it. Yes, it is close to North Korea, but the US Department of State ranks it as a travel advisory Level 1. Seoul is actually one of the safest places in Asia to visit. For reference, most European destinations including France and the United Kingdom are currently ranked Level 2 (more dangerous). This was my most expensive redemption of all 10 segments. The lesson here is: be willing to pay a premium for non-stop flights at ideal times if it matters to you. Most of the flights from Ho Chi Minh City to Seoul rely on connections, and the non-stop flights are mostly red eyes. With only a few days to spend in Seoul, I was unwilling to show up tired and lose a day of vacation. The flight cost for this segment in dollars was $863, and with the point redemption of 46,193 valued at $923, I was essentially overpaying by $60. This was close enough for me to decide to use points and save a big chunk of money.

Flight 8 (One-way Seoul to Hong Kong)

  • ICN - HKG

  • Asiana Airlines Lie-Flat Business Class on the Airbus A380 (YAS!)

  • Total Cost: Free (29,996 Chase Ultimate Rewards Points direct booking)

I am a relative aviation nerd, and part of the fun of vacations for me are the flights themselves. Especially when they are on planes that are legendary, like the Airbus A380, the world's largest passenger airliner! Airbus has put billions of dollars into developing this aircraft, and unfortunately, most of it has not been able to be recouped. They have since announced that A380 production will end by 2021 - no better time to fly this beast! Similar to previous flights, I booked this flight through Chase Ultimate Rewards directly. Cash rate for this flight was $444. 29,996 points is worth $599, so I wasn’t getting the best deal here, but it was worth it to me to be able to fly for free and still earn miles towards my United status. The lesson here is: when you book flights through the Chase Portal, they are considered cash bookings with the travel provider, therefore you still will earn your Premier Qualifying Miles (PQM). This requires the booking to be for an airline that is part of your preferred alliance (in this case, Asiana is part of Star Alliance). However, bookings that are not made directly on United’s website are NOT eligible to earn Premier Qualifying Dollars (PQD’s). In any case, I’m in need of more PQM than PQD this year to make Platinum, so it worked out just fine.

Summary

In total, the true cost of the flights I booked was $10,868 - and I paid a total of $981. A pretty damn good accomplishment, if I do say so myself.

Leveraging the tips/tricks listed below ensured that I was using my points wisely and getting the best value for my redemptions.

  • Book early. And when you see Premier Upgrade availability that matches your travel dates, book it immediately.

  • Do not avoid a city all together based on geopolitical reasons if it can get you to a region at a low cost, while still acting as a connection point to somewhere else.

  • Calculate the value of the points required to redeem, and if it is less than the cost to pay in dollars, you know you are getting a good deal.

  • Always check the flight price on the airline website directly before booking (they may have better prices than 3rd party booking sites).

  • Be willing to pay a premium (either dollars or points) for non-stop flights at ideal times if it matters to you.

  • When you book flights through the Chase Portal, they are considered cash bookings with the travel provider, therefore you still will earn your Premier Qualifying Miles (PQM’s).

I could not have done this without my Chase Ultimate Rewards Points (the most valuable currency in the travel industry, IMO). Start using a card like the Chase Sapphire Reserve today on your everyday purchases. Before you know it, you’ll be well on your way to your next dream vacation (on a budget)!