We make a family trip every year or two. For 2025, we decided to go to Costa Rica. Nine members of our family were able to make it, so this meant airline tickets and lodging for nine people! Usually, we’re able to average 96.5% of our trip costs for free. For this trip, we spent $6,259 on airfare, lounges and lodging. The cash cost if we hadn’t used points would have been $15,240. So we only got 59% of it for free. 

                                                                                      

Our total out of pocket cost for airfare, lounges and lodging was $6,259. The cash cost if we hadn’t used points would have been $15,240.

EVEN IF IT WASN’T THE USUAL 96.5% FREE, HOW DID YOU GET IT 59% OF IT FOR FREE?

Thanks for asking!

FLIGHTS:

    For the economy class flights from San Francisco to San Jose for four members of our family, I made reservations using 52,100 Avianca Lifemiles + I paid $185 in fees. Additionally, I paid $120 for a Lifemiles Lite membership (cost was $20/month for six months) in order to get a 10% discount on points redemptions. (Besides the 10% discount, I also received 3,000 miles for this). I didn’t have enough Avianca Lifemiles, so I elected to buy 121,500 miles for $1,485 (.0122222 per mile. Some of these miles were kept in reserve for future trips). I also transferred 12,000 points from Amex to Avianca Lifemiles.

Thus, my total cost for outbound airfare (SFO-SJO) for the first four persons was $636 (52,100 x .0122222) + $185 + $120= $941. 

For the return flights for those same four members, I used 52,120 Lifemiles (the portion of the purchased miles was $490) + I paid $335 in fees. My total cost was $825 for those four return tickets (SJO-SFO).

So for these four members, altogether my out of pocket cost was $1,766. If we had paid cash, the cost would have been $3,168.

For Kate and myself, we flew business class on United Airlines. Our outbound cost was 70,000 United miles + $48 (taxes). 

                                                                                                                   

Our inbound flights in business class on United Airlines cost us 70,000 United miles plus $122 (taxes). I already had 74,000 United miles so I just had to top it up by transferring 66,000 points from Chase. Our avoided cost was $3,748.

For two family members flying from Orlando: Outbound economy cost on Southwest Airlines was $429 and inbound cost was $491. We bought two $500 SWA gift cards from Costco for $860. So our net cost was $740 for what should have cost us $920.

For our ninth family member flying from DEN to SJO, they were on a UAL flight. I used $300 of United travel bank credit (see how we got this for free down below) plus I had to pay $7. So the avoided cost was $307. 

For the return flight on United, we paid $475. We did make a change to this flight and received a $268 flight credit.

Summing up, total out of pocket cost for seven round trip economy tickets and two round trip business class tickets was $2,890. The cost if we had not used any points, United travel bank credit and Costco gift cards would have been $8,350.

LODGING

                                                                                  

Our first three nights were in San Jose, the capital of Costa Rica. We stayed at the Casa Seneca. This luxurious five bedroom home had a pool and everything we could ask for. The Airbnb cost was $1,126. We used $350 of Airbnb gift cards (see how we got these for free down below) to bring our out of pocket cost down to $776.

                                                                                             

In San Jose, we hiked, went to an Animal Rescue facility, went to the National Museum and went to Hacienda y Beneficio La Chimba (a coffee plantation with a lot of art work on a 5K loop through the plantation). 

The next three nights were in La Fortuna, the adventure capital of Costa Rica. We stayed at the Arenal Family Home. This five bedroom home had a pool with a waterfall.  Unfortunately, this VRBO rental was the only five bedroom home in the area and we had to pay the full $1,293 cost. 

                                                                                                                   La Fortuna is next to the Arenal volcano and Arenal National Park. We did waterfall rappelling, white water rafting, zip lining, bird watching and crossed many hanging bridges. There was also a great swimming hole within walking distance of our home.

 

                                 

 

                                      

Our final four nights were in Playas Del Coco. We stayed in an oceanfront home right on the beach. This five bedroom home also had a pool. The cost for this four night Vacasa vacation rental was 202,500 Wyndham points. I had 103,500 points and I purchased the 99,000 additional points that I needed for $1,300. So our out of pocket cost for this rental was $1,300. If we had paid cash instead of using points, it would have cost us $3,806. 

While we were in Playas Del Coco, we went scuba diving, snorkeling, body surfing, played cards, ran on the beach and enjoyed the sunsets. 

                                      

 

                  

DINING:

  We paid cash for all of our dining except for the Tabacon restaurant and the airport lounges. In La Fortuna, we went to the Tabacon restaurant (a Hilton property) and used our free Hilton credit card credits (see info below). This covered $170 of our $350 bill.

 

LOUNGES:

 We hit the lounges in SFO, SJO (San Jose) and SAL (San Salvador). All nine of us were able to get free meals and/or drinks. This was all free due to our Priority Pass lounge access cards (received from our Amex Platinum cards). Lounge visits cost a minimum of $35 if paying out of pocket. Not all of us visited every lounge. But for those that did, for the group the value was $70 in SFO, $70 in SAL, $315 in SJO and $210 in SAL. Total $665. 

TOTALS:

Our total out of pocket cost for airfare, lounges and lodging was $6,259. The cash cost if we hadn’t used points would have been $15,240. 

 

HOW DID YOU GET THE UNITED MILES?

  We opened Chase Ink business cards and received about a half million Chase points. We then transferred 66,000 Chase points to United miles.

 

HOW DID YOU GET THE FREE AIRBNB GIFT CARDS?

   Our three Amex Business Gold cards each give us $20/month credit at Staples. On the Staples website, you can buy a $25 Airbnb gift card. So every month, we get $75 of Airbnb credit for a cost of $15. We applied this credit to our Airbnb reservation.

 

HOW DID YOU GET THE WYNDHAM POINTS FOR THE VACASA VACATION RENTAL?

Our Wyndham Business Earner cards earn 8x points for gas and 5x points for utilities. There was a 45,000 point bonus for opening the card. We only opened this card on May 22, 2023. By late 2023 we decided to take the family to Costa Rica. Vacasa had a change coming up to their vacation rental reservation program, so I needed to make the reservation before 3/31/24. Then the question became how to rack up the 202,500 points I was going to need before the program change occurred. Maximizing the 8X and 5X earning power, I did the following:. On 2/14/24, I prepaid $4,400 of electricity on my Wyndham card (earning 22,000 points). I drove to my water company and prepaid $1,200 of water on my Wyndham card (earning 6,000 points). I went to Chevron and bought $500 of Chevron gift cards on my Wyndham card (earning 4,000 points). I had previously racked up about 27,000 Wyndham points. But I was still 99,000 points short. So as previously mentioned, I purchased the 99,000 points that I needed for $1,300. Altogether, this gave me the 202,500 points I needed. 

I mention the dates because if I had had more time, I wouldn’t have needed to buy any points. 

 

HOW DID YOU GET THE UNITED TRAVEL BANK CASH?

Our Amex Platinum cards and our Amex Business Platinum cards each give us $200 of airline credit per year. Our Chase Ritz-Carlton card gives us $300 of airline credit per year. We use all of these cards to buy United Travel Bank cash. 

 

HOW DID YOU GET THE FREE HILTON CREDITS TO USE FOR DINING?

Our Amex Hilton Surpass card gives us a $50 credit per quarter at Hilton properties. Our Amex Business Hilton Honors cards give us a $60 credit per quarter at Hilton properties. We also have $200 of semi-annual credit with the Hilton Aspire card and several hundred dollars of Hilton gift cards. But these are not accepted at all Hilton properties and unfortunately we weren’t able to use them at the Tabacon restaurant. 

 

COULD WE HAVE USED POINTS TO MAKE THE TRIP ENTIRELY FREE (other than taxes)?

Absolutely! We could have a) Cashed in credit card points for cash and used straight up cash to pay for the VRBO rental, Southwest flights and everything else; or b) For the flights that we had paid cash for we could have booked flights that required a ridiculous amount of points. And for the lodging we could have booked a bank of five hotel rooms in each city. But this would have also used up a ridiculous amount of points. So it would have been an enormously poor value to use points for the expenses that we paid cash for.