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

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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.

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:

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.

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.

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“. 

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.

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.

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.

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!

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.

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.

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:

• 70,000 Marriott points per night for the Ritz-Carlton Grand Cayman
• 45,000 Marriott points per night for the Grand Cayman Marriott Beach Resort
• 12,000 Starwood points per night for the Westin Grand Cayman Seven Mile Beach Resort and Spa

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!

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:

• 70,000 Marriott points per night for the Ritz-Carlton Grand Cayman
• 45,000 Marriott points per night for the Grand Cayman Marriott Beach Resort
• 12,000 Starwood points per night for the Westin Grand Cayman Seven Mile Beach Resort and Spa

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!