March - 2017



2 Round trip tickets from SFO-HNL

  • Virgin Atlantic Card (25,000 mile sign-up bonus)

  • Virgin America Visa Premium & Signature Cards (15,000 & 10,000 point sign-up bonuses)


Ticket 1: Before its merger with Alaska Airlines, Virgin America (VX) was a partner airline of Virgin Atlantic.  I called Virgin Atlantic and was able to cash in my 25,000 points for a round trip ticket on VX.


Ticket 2: Used 20,000 VX points online to redeem a round trip ticket on the same flight as Ticket 1.


If we paid cash it would have been $380 per person, $760 total.  Instead, it was 45,000 points and $22 in fees for both tickets.


We also decided to do a day trip from Oahu to Kauai; luckily, VX was still a partner with Hawaiian at the time. By calling VX, we were able to use our leftover points (6,000 per person) for round trip tickets between Honolulu and Lihue.  If you do the math above, we got 25,000 points with sign-up bonuses from the Virgin America cards but only used 20,000 for the flight from SFO to HNL.  This leaves 5,000 points, so where did we get the extra 7,000 needed for our flights to Kauai?  We racked up more points by everyday spending on things like car repairs, furniture, and medical expenses.


If we paid cash, the Kauai flight would have been $180 per person, $360 total.  Instead, it was 12,000 points and $12 in fees for both tickets.


Hotel: We paid cash for an Airbnb on Oahu (got 3 points per $1 spent with the Chase Sapphire Reserve because it codes as travel)


Car Rental


One weekly rental on Oahu 

  • 2,750 Hertz Gold Reward Points

  • $520 if paying cash


We racked up a ton of e-rewards by doing a lot of surveys and cashed them out for 2,750 Hertz Gold Plus Rewards. One thing to remember is that all your points need to be in one account when redeeming for a rental. We had the 2,750 split between accounts, but luckily Hertz lets you transfer points among family for free so it only took a quick phone call to consolidate our points.


If we paid cash the rental would have been $640 for the week.  Instead, it was 2,750 points and $120 in fees.


Trip Award Summary 

  • 2 Round-trip tickets from SFO-HNL

  • 2 Round-trip tickets from HNL-LIH (Kauai day-trip)

  • One week car rental on Oahu


Cost using points: 59,750 points & $154 in fees

Cash Value: $1,606 (I subtracted the fees since they still had to be paid)  

Venice Beach

August - 2017


1 Round trip ticket from SFO-LGB (booked 2 months in advance)

  • 8,900 Jet Blue points transferred from Amex Membership Rewards

  • Ticket would have cost $147 if paid in cash

Usually you get 1 Jet Blue point for every 1.25 Amex point when transferring, but Amex was offering a bonus at the time and they thankfully transferred over at a 1:1 ratio. 


Trip Award Summary 

  • 1 Round-trip ticket from SFO-LGB

Cost using points: 7,340 points & $11 in fees

Cash Value: $136

Charleston, SC

November - 2017


2 Round trip ticket from SFO-CHS

  • 50,000 Flying Blue miles (booked 10 months in advance)

  • Tickets would have cost $403 each ($806 total) if paid in cash


We did a flight search and found the best route on Delta Airlines which is part of the SkyTeam alliance so you can buy your tickets through Flying Blue.  Their award ticket search engine is one of my favorites due to its accuracy and user friendliness.  Even better, you can transfer points to them from both Amex and Chase, we decided to do a little of both to spread it out a bit.

Car Rental


One premium weekly rental in Charleston 

  • 2,750 Hertz Gold Reward Points​

  • $502 if paying cash

The U.S. Travel Association recently brought back Daily Getaways, where you can purchase travel at a pretty good discount.  One of the offers that we chose was 13,200 Hertz points for $560, so each point is worth $0.042.


For the rental I can either pay entirely in cash for $502 or use 2,750 points + $72 in fees.  If you subtract the fees from the $502 cash value you get a $430 base price which I'm using 2,750 points for instead.  Remember, I paid $0.042 for each of those points, 2,750 x $0.042 = $115.50. So by taking advantage of the Daily Getaway offer I save $315 for this rental.   


Trip Award Summary  

  • 2 Round-trip ticket from SFO-CHS

  • One weekly rental in Charleston, SC

Cost using points: 52,750 points & $94 in fees

Cash Value: $1,214

Portland, OR

August - 2017


1 Round trip ticket from SFO-PDX

  • 7,340 Southwest Rapid Reward points transferred from Chase

  • Ticket would have cost $138 if paid in cash  

Trip Award Summary 

  • 1 Round-trip ticket from SFO-PDX

Cost using points: 7,340 points & $11 in fees

Cash Value: $127

New York City

June - 2018


2 tickets from SFO-EWR

  • 12,500 AAdvantage miles (per person) earned with the Aviator Red Mastercard

  • Tickets would have cost $271 each if paid in cash  

2 tickets from JFK-SFO in lie-flat business class

  • 11,200 Chase Ultimate Rewards + 15,000 AAdvantage miles per person

  • Tickets would have cost $1,450 per person 

JFK-SFO is one of the flagship routes for American Airlines, meaning that they use a nicer plane than the rest of their domestic routes.  The business class seats came with bedding materials and reclined completely flat.  Top-notch food along with noise-cancelling headphones were some of the other perks too.  

To book these seats, I searched for availability on American's website but couldn't find any.  Every once in a while, they offer upgrade space for economy tickets, and that happened to open up right when I needed it to.  So we used 11,200 Chase points for each economy ticket then upgraded to business for 15,000 American miles. Also, having the Aviator card got me a 10% rebate on points used for flights so we got 1,500 points back for the flight to New York and 2,500 for the flight home to SFO.  

Rental Car:

1 day rental to drive upstate New York

  • 675 Hertz Gold Reward Points​

  • $84 if paying cash

Public Transportation

2 unlimited metro passes for 7 days

  • 2,200 US Bank Flex Perks points per person

  • $33 if paid in cash

The US Bank Flex Perks Visa card let's you make a travel purchase whenever you want then sends you a text message giving you the option to use points instead of cash.  Public transportation counts as travel.

Trip Award Summary 

  • 2 coach tickets from SFO-EWR

  • 2 business class tickets from JFK-SFO

  • 1 day rental car 

  • 2 unlimited 7 day metro passes

Cost using points: 54,575 points & $22 in fees

Cash Value: $3,626


August - 2018


2 first class round-trip tickets OAK-LIH (Kauai) then HNL (Oahu) - SFO

  • Paid $2,190 for both tickets on Hawaiian Airlines.  I used this purchase to meet the minimum spend for our Hyatt Card which then helped us stay for free at the Grand Hyatt Poipu in Kauai.  It also means that we earned a ton of miles for our flights since we paid with cash. 

Using points to fly first class on Hawaiian Airlines is not easy, they usually want approximately 80,000 points each way.  You could transfer from American Express Membership rewards but I think this is a bad deal for a 5 hour flight.  It worked out that we could use the airfare to make the minimum spend for the Hyatt card.  

2 tickets from LIH-HNL (inter-island flight from Kauai to Oahu)

  • 11,133 US Bank Flex Perks points

  • Tickets would have cost $167 per person 


3 Nights at the Grand Hyatt Poipu 

  • 75,000 Hyatt points

  • Room would have cost $1,686 is paid in cash 

The Hyatt Card earned us 40,000 points.  Since we needed 75,00 we transferred the remaining 35,000 from Chase to Hyatt and made the reservation. 

Rental Cars:

3 day rental in Kauai

  • 2,025 Hertz Gold Reward Points​ + $42 in fees  

  • $213 if paying cash

7 day rental in Oahu

  • 2,750 Hertz Gold Reward Points​ + $55 in fees

  • $470 if paying cash

Trip Award Summary 

  • 2 inter-island tickets

  • 3 nights in luxury hotel 

  • 10 rental car days 

Cost using points: 102,041 points & $108 in fees

Cash Value: $2,606

Paying cash for our flights to and from the mainland allowed us to earn about 8,000 points each which we can use for future trips back to Hawaii.

Houston, TX

March - 2019


2 tickets from SFO-IAH (Houston)

  • 12,500 points + $5.60 in fees for United Airlines (bought through Singapore Airlines) 

  • Ticket would have cost $252 if paid in cash  

United wanted 18,000 points for this flight.  Since United Airlines and Singapore Airlines are partners, the latter was offering the same flight for 12,500 points each.  We were able to transfer our Chase points to Singapore and purchase the tickets at the lower rate.

Unfortunately, the flight home did not have any availability with Singapore so we booked directly through the Chase travel portal.

2 tickets from IAH-SFO

  • 17,233 Chase UR points + $5.60 per person

  • $260 if paid in cash


We stayed with friends for the first few days and switched to a hotel for the last two nights.

2 Nights at the Le Meridien in Downtown Houston

  • 17,000 Chase UR points

  • $255 if paid in cash

Rental Car:

4 Day Rental

  • 2,700 hertz points + $81 in fees

  • $389 if paid in cash

Trip Award Summary 

  • 2 Round-trip tickets from SFO-IAH

  • 2 Nights in a hotel

  • 4 rental car days

Cost using points: 81,066 points & $103 in fees

Cash Value: $1,322