Saving $1000 with United Miles: Natalya’s trip to Grand Cayman and Cancun
Read about how Natalya saved $1000 on tickets to Grand Cayman and Cancun and got the most convenient flights by using 52.5k United Mileage Plus miles and some clever trip planning!
Natalya wanted to go to Grand Cayman and Cancun to join me and Svetlana. I already wrote about how I got to Grand Cayman with miles and Svetlana’s, aka Samba For Miles, route is coming soon. Natalya lives in San Francisco, which is a long way to the Caribbean, but she really really loves the beaches!
Our trip dates were:
- Grand Cayman: Nov 22 (Thanksgiving Thursday) to Nov 25 (Sunday after Thanksgiving)
- Cancun: Feb 15 to Feb 19 (President’s day weekend)
At the time we looked in October, round-trip tickets from San Francisco to Grand Cayman cost $850 (with two stops on the way back!!!) and about $600 to Cancun. So that’s $1450 total… a bit steep… fortunately, she had United Mileage Plus miles! We used option five on my Top Five Ways to Fly to the Caribbean with Miles.
Stopover and Open Jaw on United Mileage Plus
United Airlines international round-trip awards allow a stopover and two open jaws. Unlike with American Airlines, the Caribbean is considered an international award!
This means: If you take two trips to the Caribbean, you can book 3 out of 4 legs as one round-trip United award!
Here were the minimum award prices on United Mileage Plus for Natalya’s 4 legs:
SFO – Grand Cayman: 35k miles in Standard Economy
Grand Cayman – SFO: Nothing available, but 35k Standard Economy for elites or holders of United Explorer Card
SFO – Cancun: 30k miles in Saver Business, 35k miles in Standard Economy
Cancun – SFO: 17.5k miles in Saver Economy
Important Note: If you are elite on United or have the United Explorer Card and are paying for a Standard Award, you can have *any* tickets on United that is on sale.
When redeeming a round-trip, it makes sense to combine two of these legs into one and that’s exactly what we did! Natalya can fly from Grand Cayman to Cancun routing through Houston, San Francisco (where she will stopover from Nov 25, 2012 to Feb 14, 2012) and New York.
There actually was a direct flight from San Francisco to Cancun on February 15, but it arrived at 5 pm so she decided to leave the night before to have a full day in the sun! … and also spend more time flying with me from New York!

Her one round-trip was the following:
- Outbound: Grand Cayman – Houston – San Francisco (stopover from November 25 to February 14) – New York – Cancun for 35k miles
- Inbound: Cancun – Los Angeles – San Francisco on February 19 for 17.5k miles
How is this a roundtrip, you ask?
Well, as I said, United allows a stopover and two open jaws. Here, the trip starts in Grand Cayman and the destination is Cancun. This is only the first part of the trip. We can just pretend she lives in Grand Cayman… wouldn’t that be nice! On the way to Cancun, she is stopping in San Francisco (using the one stopover). On the return leg of her journey, she is returning from Cancun to San Francisco. Since she started in Grand Cayman and is returning to San Francisco, this uses one of her two allowed open jaws. The outbound and inbound leg make one roundtrip!
The total cost for the above two leg trip is 52.5k UA miles + taxes. She also needed a ticket to Grand Cayman, which would have cost 35k miles or $350 on American Airlines; at that price, it’s better to spend money than miles plus she’d be luckily catching the American Airlines double miles promotion!
We are going to Cancun in two weeks… and Tatyana is coming too (don’t worry, you’ll hear about her miles route too!) it will be a relaxing vacation with the four of us… let’s have a toast to that!

Summary
- Natalya spent 52.5k miles + $450 on roundtrip tickets to Grand Cayman over Thanksgiving and Cancun over President’s Day Weekend
- These would have cost her a minimum of $1450 and she would have had to make two stops flying from Grand Cayman to San Francisco.
- She optimized miles by using a Standard Award on United and combining the trips from Grand Cayman to San Francisco and San Francisco to Cancun into one leg. She was able to choose any flight United Airlines had for sale and use the most convenient flights.
God help me, I put aside a whole afternoon to firgue this out.
Your site is so helpful thank you! I just started racking up points in the last 6 months and had no idea these stopover/openjaw options made the points so much more valuable!
I’m getting ready to book a roundtrip from the mainland to Hawaii on United, and I really want to take advantage of this opportunity! I already have 2 roundtrip tickets from my home airport (RDU) booked for before my Hawaii trip (in Nov), but I’m wondering if I can cancel part of these itineraries (they are refundable southwest fares) and book using my United open jaws/stopovers. I have been puzzling over this for hours, but I can’t figure out if I am getting this right. So I live near RDU, and I have roundtrips scheduled in August to SEA and in October to LAX. In November I want to fly from RDU to Honolulu and from Kauai back to RDU.
Can I book something like:
Plan A (this would save me two one-way tickets)
Depart SEA/Arrive RDU
Depart LAX/Arrive RDU
[stopover RDU]
Depart RDU/Arrive Honolulu
Depart Kauai/Arrive RDU
Plan B (only saves 1 one-way ticket)
Depart SEA/Arrive RDU
[stopover RDU]
Depart RDU/Arrive Honolulu
Depart Kauai/Arrive RDU
Plan C (I am pretty sure this would work but I’d rather save a leg of the Seattle trip since that ticket was pricier)
Depart RDU/Arrive LAX
[stopover LAX]
Depart LAX/Arrive Honolulu
Depart Kauai/Arrive RDU
???
Glad you’re having a try at maximizing United miles and you definitely have some good ideas! :)
Your first one won’t work. You have at least two stopovers and probably three open jaws if you count them.
The second one works. One stopover and two open jaws.
The third one works too… as you already said :)
Just keep in mind the United website may not price these and you will have to call in and give them your flight numbers.
does this still work after the changes this year to United?
Thx.
Yes, it does!