Ask an Award Booker: “How Can I Book Flights to Grand Cayman for My Family of Four?”

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Ask an Award Booker: “How Can I Book Flights to Grand Cayman for My Family of Four?”

Million Mile SecretsAsk an Award Booker: “How Can I Book Flights to Grand Cayman for My Family of Four?”Million Mile Secrets Team

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We’re trying something new!   Our award booker posts will answer a reader’s specific award booking question and show folks exactly how to find and book a similar trip.  

We can’t wait to answer your questions and get you Big Travel with your hard-earned miles & points!

If you’d like us to consider your question, please leave a comment on this post and we’ll try to help you out!  The more details you can provide (types and amounts of miles & points you have, number of passengers, routing, time of year, etc.) the better.  We can’t promise we’ll get to everyone, but we’ll do our best to solve as many award booking challenges as we can.

Today’s question comes from Todd, who commented:

We’re a family of 4 looking to fly from Myrtle Beach to Grand Cayman.  I have 75,000 American Airlines miles, 89,000 Delta miles, 37,000 Alaska Airlines miles, 81,000 Starwood points, 320,000 Marriott points, and 40,000 Citi ThankYou points.  What airlines and partnerships are the best use of points?

The Cayman Islands are very expensive, so using miles to fly there and to stay for free at a hotel is a great way to save!  I’ll show you how to search for flights and get the most value out of your miles.

Flights To Grand Cayman
Todd Can Visit the Beautiful Seven Mile Beach Using Miles!

How Do You Book Flights to Grand Cayman for a Family of Four?

Link:   American Airlines Award Chart

Link:   Alaska Airlines Award Chart

Link:   United Airlines Award Chart

Fortunately, the Cayman Islands aren’t far, and several airlines fly there.  The first thing I’d do is look at the airlines that fly out of your home airport.  Wikipedia maintains accurate lists of airports and destinations and is a great tool when building an award booking.

If we look at the Myrtle Beach Airport Wikipedia page, we can see that no airline flies direct to Grand Cayman:

Flights To Grand Cayman
Wikipedia Is a Great Resource for Helping Plan Award Travel

Next, take a look at the Wikipedia list for the Grand Cayman Airport, and cross-reference any airport that matches the list from Myrtle Beach.  If the cities match, it means you can fly with one connection to Grand Cayman.  In this case, you could connect in:

  • Charlotte on American Airlines
  • Dallas on American Airlines
  • Philadelphia on American Airlines
  • Atlanta on Delta
  • Detroit on Delta
  • Newark on United Airlines
  • Chicago on United Airlines

Next, we need to figure out in which programs you hold sufficient miles to book one of these flights.

You can use American Airlines and Alaska Airlines miles to book American Airlines, and you can convert Marriott or Starwood points into United Airlines miles to book on United Airlines.  Or book Delta flights with Delta miles.

American Airlines charges 15,000 miles per person in coach each way for travel from the United States to Grand Cayman, but only 12,500 miles during off-peak season.  For travel to the Caribbean, off-peak season is September 7 to November 14, and April 27 to May 20.  Alaska Airlines charges 17,500 miles for the same flights.

Delta no longer publishes an award chart, but if you use their award search engine, the lowest price is 20,000 miles per person each way.  Finally, United Airlines charges 17,500 miles per person each way.

You have enough miles to book American Airlines one way, and Delta the other way.

Check out this video guide to see how you can book flights to Grand Cayman and a hotel stay using miles & points!






How to Book Flights to Grand Cayman Using American Airlines Miles

Step 1.   Navigate to the American Airlines Website

Go to the American Airlines website.  You’re not required to sign-in if you’re just searching and aren’t ready to book yet.

Step 2.   Enter Your Trip Details

Enter your preferred departure date, return date, how many passengers you want to book, and your departure and return cities.  Be sure to click the “Redeem Miles” checkbox too!

When everything is filled in, click the blue “Search” button.

Flights To Grand Cayman
Don’t Forget to Check “Redeem Miles”

Step 3.   Look for Saver Award Seats

At the top of the screen you’ll see a row of 4 boxes.  You will want to look for your booking class followed by “MileSAAver”.  These are the lowest priced awards.  Click on the class of service you want (in this case, “Economy MileSAAver).

Step 4.   Find Available Dates

The row of dates below the bar will show all available days with saver award seats.  If your class is available, the date will be highlighted in the same color as the button above and display the number of miles required for a one-way flight.

For example, a coach saver date will light up in green and display “15K”.  That means a one-way flight is available for 15,000 American Airlines miles.  If you’re booking during off-peak season, look for coach saver seats with the display “12.5K“. 

Flights To Grand Cayman
Find Dates With Available Seats in Your Desired Class of Service

Step 5.   Pick Your Outbound Flight Dates

Click on the day you’d like to book to select your outbound flight.

Note:   If you can’t find available flights on the dates shown, click the left and right arrows on the sides of the availability calendar.  It will show you another week of dates!  Or click “Show Full Calendar” to view 30 days of available dates.

Then, scroll to the bottom of the page and click the gray “Continue” button.

Step 6.   Choose Your Flights

You can now select your flights!  Look towards the center of the page and find your preferred outbound flight.  Click the “Flight Details” button to view connection times and more information.

Add the flight you want to your itinerary by clicking on it.

Flights To Grand Cayman
Select Your Flights at the Lowest Award Level

Step 7.   Sign Into Your Account and Complete Booking

Scroll to the bottom of the page and you will see a sign-in form.  Enter your American Airlines credentials and click the red “Log In” button.

Click the red “Continue” button on the page to be brought to the booking screen.  Then, enter the requested information on the booking page and press the blue “Continue button at the bottom of the page to be brought to the payment page.

Flights To Grand Cayman
All That’s Left to Do Is Pay for Your Ticket!

Enter your payment button and click the red “Book” button at the bottom of the page.

How to Book Flights to Grand Cayman Using Delta Miles

Step 1.   Navigate to the Delta Website

Go to the Delta website.  You’re not required to sign-in if you’re just searching and aren’t ready to book yet.

Step 2.   Enter Your Trip Details

Enter your preferred departure date, return date, how many passengers you want to book, and your departure and return cities.  Make sure to select “Show Price in Miles” and “Flexible Days“.

When everything is filled in, click the blue “Find Flights” button!

Flights To Grand Cayman
Make Sure to Select “Show Price in Miles”!

Step 3.   Look for Lowest Rate

Delta does not have an award chart, so you should look for the lowest rate you can find.  The lowest price will display in orange, while more expensive prices will display in blue.

From Grand Cayman to Myrtle Beach, the lowest price Delta charges is 20,000 miles one-way.  Select which day you want to display flight options.

Flights To Grand Cayman
Find the Lowest Prices by Searching for Your Desired Travel Dates

Step 4.   Select Your Preferred Flight

Select which flight option you want, but make sure it’s at the low rate, because higher cost award seats may also show on the list of available flights.

Flights To Grand Cayman
Make Sure the Lowest Price Shows Prior to Booking

Step 5.   Book Your Tickets

After selecting your flights, you’ll need to sign into your Delta account, enter passenger information, and pay for your ticket.

How to Book Hotels in the Cayman Islands Using Points

Hotels in the Cayman Islands are notoriously expensive, and can easily run over $1,000 a day!  But because you have Starwood and Marriott points, which you can transfer between programs, you have a couple of options for hotels:

All 3 hotels are located on Seven Mile Beach, and the Westin Grand Cayman Seven Mile Beach Resort and Spa is by far the best deal.  Because Starwood points convert at a 1:3 ratio to Marriott points, it’s like paying 36,000 Marriott points a night!  And when you book a category 3 to 7 hotel using Starwood points, you get the 5th night free.

So a 5-night stay at the category 5 Westin Grand Cayman Seven Mile Beach Resort and Spa would only cost 48,000 Starwood points (4 nights X 12,000 Starwood points per night plus 5th night free) instead of $3,763!

Flights To Grand Cayman
Hotels in Grand Cayman Are Expensive and a Great Use of Points!

Because you have enough points to fly everyone to and from Grand Cayman, you don’t need to look at the Marriott Travel Packages, which gives you airline miles and a free hotel stay.  However, because the Ritz-Carlton is a Tier 5 hotel, and the Marriott is a Category 9 resort, you would need to redeem a minimum of 320,000 Marriott points to earn a week stay at the Marriott and 55,000 United Airlines miles, or 470,000 Marriott points to stay at the Ritz-Carlton.

And because Starwood’s Nights and Flights program only allows hotel bookings up to Category 4 properties, and the Westin Grand Cayman is a Category 5 property, you can’t use this program in the Cayman Islands.

Recap:  How to Book Flights to Grand Cayman

The Cayman Islands are beautiful and absolutely worth the trip.  Further, there are plenty of options to get there using miles from Myrtle Beach, although you’ll have to connect through:

  • Charlotte on American Airlines
  • Dallas on American Airlines
  • Philadelphia on American Airlines
  • Atlanta on Delta
  • Detroit on Delta
  • Newark on United Airlines
  • Chicago on United Airlines

You’ve also got very nice hotel options you can book using Marriott points or Starwood points:

When planning award travel, you should investigate all the options available to you and determine what gives you the most value based on cost and quality.

Thanks for the question, Todd!  Let us know what you decide to book!

Have an award you want to book?  Leave a comment below and your question may be featured in our award booking series!

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Editorial Note: We're the Million Mile Secrets team. And we're proud of our content, opinions and analysis, and of our reader's comments. These haven’t been reviewed, approved or endorsed by any of the airlines, hotels, or credit card issuers which we often write about. And that’s just how we like it! :)

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Thanks so much for this super offer! My husband and I have been collecting points but we aren’t sure how to best redeem them. We’re going to a wedding on the Jersey shore in May and are contemplating something like: Sea-Tac to Newark May 22; Newark to Quebec May 28; Quebec to any NYC airport June 4; any NYC airport to Sea-Tac June 7. We have 374,000 Chase Ultimate Rewards, 95,000 combined Alaska points (both of our accounts) and one Companion fare; 43,500 Best Western points; 5,000 Hyatt points. We’re booked into a Marriott for the wedding and will stay with a friend in NYC but are totally open re: where to stay in Quebec. Thanks so much for your help!

Ah, should have added that my husband isn’t very comfortable flying so we’d like to fly first class, if possible, at least for the coast-to-coast flights.

Million Mile Secrets

Sounds like an amazing trip, Caroline! We’ll try to come up with something for you soon.


Thank you for taking my question and answering it so clearly. I have booked the flights for Aug. and the Westin Grand Cayman with SPG to save a few more points. Our greatest fear as points followers of yours is to not score the best redemption on points. This time it was not so tricky, but using partner airlines is where we all seem to get lost. Thank you again for all of your help, the flights are booked and the hotel is next, they have lots of avilability!!!

Million Mile Secrets

Awesome, Todd! I hope you and your family have an excellent time!

Go to Travel Gal

My advice would be to drive yourself to Ft. Lauderdale and book a super cheap flight to Grand Cayman on Southwest. We booked recently for ~4,200 points round-trip per person. We took a super cheap flight on a discount airline to get ourselves from Indy to FLL.

Million Mile Secrets

Thanks for helping out, Lyn! That’s a really cheap option for folks who are willing to get to Fort Lauderdale!

1 king bed? Priced for 1 occupant? How does the math work if you are trying to book a room that will accommodate the whole family?

Million Mile Secrets

Hi Sarah, you can book a room with 2 doubles for the same price in points.

This is so helpful!! Thank you! Gave me some great ideas. My only question is are there limitations on how many reward tickets I can book in this way? For instance, if I had enough points for my entire (5 person) family, can I book 5 reward tickets?

Million Mile Secrets

You can use these tips to book the same trip for 5 people. You’ll just have to find 5 open award seats on a single flight or break up the group over different flights.

Is that realistic to expect to book 5 award seats? Or should I expect to book two different flights? I’ve just never booked award travel for the whole family before! I’m excited to try it soon though 😀

Million Mile Secrets

It depends on the route and airline, but if you’re flexible with travel dates, you can usually find multiple low-level Saver award seats. Let us know if you need any help!

Million Mile Secrets

Hi Sandra – Glad to hear you’re enjoying the series!

Using British Airways Avios points for short-haul flights to the Caribbean is a good strategy from Charlotte.

Check out the Avios map tool from Wandering Aramean to get an idea of award pricing (for example, Cancun, Nassau, Turks & Caicos, and Grand Cayman are all 7,500 British Airways Avios points one-way in coach:

Hope this helps!

This article was one of the best on MMM! To be honest, I’ve felt for a while that this website does nothing but only promote CC’s (so that commission is earned), but I’m totally impressed with this article. We need more of such practical examples.
So, here’s my question. We usually travel to Europe in summer and therefore we try not use AA miles for other trips unless we need to.
My kids have been asking to go somewhere to the beach during this winter break. Since we’ve never traveled south outside the USA, I don’t know which places would be safe, affordable, and cultural. We’d love to see some of the local sights (preferably w/out renting a car) besides spending the entire time on a beach and within resort/hotel’s walls. We live in Charlotte (CLT). Would you have destination suggestions for a family of four (2 parents and two 10/12 year olds) with very very minimal Spanish?
So, we’re based in CLT. Winter break would be sometime Dec.17-Jan.1, 2019.
These are the current point/miles balances.
AA FF miles: 340k + 320k (2 accounts), but like I said we’d prefer not use unless it’s needed (unpractical or expensive on the other programs).
BA Avios Household account: 303K avios (we’d prefer to use these points).
Alaskan Miles: 91k + 94,500 (2 accounts).
IHG points: 45k+1 FREE annual night and 94K in the 2nd account.
Marriott: 73k points.
Hilton: 104k + 44k (2 accounts.
If affordable, we don’t mind to pay cash for some nights for hotel or AirBnB.

Any advice, suggestions would be appreciated.

I’d like to add that I should get my annual FREE night from my Marriott CC in June’18. Thanks