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  • Sean Cheyney

How Can This Family of 5 Afford It?

2 weeks half-way around the world for less than $2000 in transportation and lodging


After several epic family trips (like our Australia trip) I get all kinds of questions from people whenever I share our family travel stories:


Are you guys rich? Hardly


Do you go into debt and max out credit cards? Nope, not at all


Do you work for an airline or hotel chain? I used to be a bartender part-time at a Hyatt near my house, but haven’t done that in more than 5 years.


Are you getting compensation for reviews or free tickets from the airline? I wish, but no


Can you teach me how you were able to make this happen? Yes, keep reading and I’ll share the strategies and careful planning I used to make this trip happen.


Where are all of the points coming from?


Everyone wants to know how we accumulate all of the points needed to take a family of 5 on some pretty fantastic trips. I have been fascinated (and a little obsessed at times) with travel hacking, and the ability to get points on activities I am doing anyway. It just takes a little organization, education, and discipline to maximize points and miles to your accounts.


To be fully transparent, I do travel for work, but with the pandemic the last couple of years, work travel was non-existent for me. I didn’t take a single work trip in 2020, and didn’t take my first work trip in 2021 until June. I only tallied 6 total work trips last year, although I expect more in 2022 (fingers crossed – please let the COVID situation get better this year!).


Also, keep in mind that we didn’t use any American Airlines miles or Chase Ultimate Rewards points for 2 years (Costa Rica trip), and we didn’t use any Marriott points or Amex points for 3 years (since our Australia trip), so they had time to accumulate.


The majority of our points and miles are coming from 3 activities (70%):

  • Credit card usage – strategic spends by type on various cards

  • Credit card sign up bonuses

  • Credit Card usage offers (Amex Offers for example) and travel shopping portals (like AAdvantage eShopping)


The remaining 30% come from actual airline travel and hotel stays. In 2020 and 2021, a much lower percentage came from travel activities.


Below is exactly what we did to accumulate points and miles over the past 2 years:


New credit cards I signed up for in the past 2 years:


Credit card usage (I have a few other cards, but the ones below account for 90% of spend):

  • Hilton Amex – We use this exclusively for gas and groceries, earning 6x points per dollar.

  • Marriott Amex – We have this tied to Amazon, but otherwise, we’ve moved away from this card for everyday purchases. I use either this card or the Marriott Business Amex when staying at or dining at Marriott properties.

  • Chase Sapphire Reserve – This is generally our go-to default card because the Chase Ultimate Rewards are flexible / versatile and give you 50% more when using the Chase travel portal to book flights. Also, it is always used for dining out because of the 3x points per dollar.

  • Chase Ink Business – There are a few categories (like mobile phone) where you earn multiple points per dollar. Any Chase Ultimate Rewards points can be combined with the ones from the Chase Sapphire Reserve and still give you 50% more with the travel portal.

  • American Express Platinum – We use this one more and more, but the big areas here that rack up the points are:

  • 5x points per dollar when booking flights directly with the airline or through the American Express travel portal.

  • Amex Offers – tons here with a variety of stores, restaurants, and services, that will give you either bonus points or multiples on your store spend (like 5x points for Amazon spend up to a certain amount).

Credit Card spend incentives:

  • Shopping portals: Whenever we need to make any purchase online (clothes, sports equipment, dog food, electronics, etc…), we first check to see if the store is part of any of the shopping portals we use (mostly Chase, Amex, or Aadvantage eShopping). If they are, then we use the click through link. Sometimes I am able to stack bonuses. A good example is when a store is also part of an active Amex offer. If using the Aadvantage portal, then I can earn both AA miles and Amex points in addition to the normal points I would get for using the Amex Platinum card.

  • Amex Offers yielded me a lot of points over the past 2 years simply by adding them to my card, and then using that Platinum card whenever I need to use a card for that store or service.

  • Most of my work travel and a couple of short family getaways (although admittedly not much over the past 2 years) was on American Airlines and other OneWorld partners (Finnair and British Airlines for example). Hotel stays varied but were mostly spread across Marriott, Hilton, and IHG properties.


How were the points and miles used?


For this trip to Thailand, we used points / miles from the following sources to cover transportation / lodging:


  • American Airlines miles

  • Chase Ultimate Rewards points

  • American Express points

  • Marriott points

  • Uber credits


Below is exactly how we redeemed points and miles:


  • American Airlines miles – On the way to Bangkok, we flew Japan Airlines (JAL) in economy class. For 2 of us, I used flight vouchers from getting bumped that (thanks to pandemic related date extensions) hadn’t expired yet. That covered $1300 for the one-way trip for 2. For the other 3, I was able to get a redemption of 35,000 per person for 105,000 miles. In addition, we paid $100 in taxes. On the way home, we used 37,500 miles per person for all 5 of us for a redemption of 187,500 miles and $150 in taxes. Total roundtrip = 292,500 miles + $1300 in free vouchers + $250 in taxes. Total savings = $10,500 ($650 x 5 for outbound + $1450 x 5 for return based on ticket price at time of booking).

  • Chase Ultimate Rewards Points – I used 150,000 points + $40 for our flights from Chiang Mai to Phuket and Phuket to Bangkok. Total savings = $2350

  • American Express points – I used 100,000 points + $50 for 2 rooms for 4 nights each (total of 8 room nights) at the Shangri-La hotel in Chiang Mai. I actually paid $250 out of pocket but the Amex Platinum has a $200 annual luxury hotel credit, which was triggered with the booking, so I got a $200 statement credit lowering my out of pocket to $50. Total savings = $1250

  • Marriott points = I used 400,000 points + $270 for 2 rooms for 6 nights each at the Le Meridien Phuket (one of them upgraded, which is the reason for the extra $270) for a total of 12 room nights. What I like about Marriott is that when you redeem points and stay 5 nights, the 6th night is free. Total savings = $3,672.

  • Uber credits – I used $40 in credits ($30 from the December Platinum Amex credit and $10 from usage credits) + $10 for our ride to the airport to start our trip.

Total Savings = $17,822


I also spent out of pocket for a few travel related expenses:


  • Flight from Bangkok to Chiang Mai: It was only $232 for the 5 of us on Thai Smile, so I paid out of pocket. I booked directly with the airline, using the Amex Platinum, so I earned 1,160 Amex points.

  • Hotel in Bangkok: Even though we stayed at a Marriott property (Royal Orchid) for 2 nights (2 rooms for 4 total room nights), the first night had to be paid for under the Thailand government’s Test & Go program (started on November 1st), which didn’t qualify for points redemption. It included pickup from the airport and PCR testing at the hospital (drive through), and the extra $20 per person to get the results back in under 6 hours (totally worth the extra $100). The Test & Go is for one night, but the hotel night was cheap for the second night, so I opted to pay instead of using points.

Total spend = $654


Ground transportation:

Airport transfers: I did something I’ve never done before, which is to arrange ground transportation with the hotel for pickup and drop off back at the airport. When I priced it out, it actually ended up either equal to or less expensive than other ground transportation companies. For pure convenience (we need a van which is usually harder to find) and feeling like you are on vacation, there is nothing like walking out of baggage claim to find someone holding a sign with your name on it. For drop off at Bangkok, roundtrip in Chiang Mai, and roundtrip in Phuket,

Total spend = $175


Other ground transportation (taxi, tuk-tuk):

I recommend using the Grab app (similar to Uber), which is what we used across Thailand eight times for $112. Additionally, we spent $30 on a taxi and $30 on tuk-tuks.

Total spend = $172


So, if we are keeping score:

  • Total transportation and lodging related out of pocket costs = $1,853

  • Total transportation and lodging related savings with points and miles = $17,822

  • Total value of lodging and transportation if the whole things was out of pocket = $19,675

  • Cost % compared with value = 9.4%

The reason I shared the difference between the value and what we actually paid is to show that if we had to pay nearly $20,000 for lodging and transportation, this trip would have been way out of our budget and wouldn’t have happened.



Relax, in upcoming posts, I’ll share my methods for getting organized with points overall, spend categories, and making the most efficient use of points and miles when traveling.

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