Weekend Getaway is a new series by 10xTravel that walks you through a few different ways to book a weekend getaway to popular destinations using points and miles. Today’s piece takes us to Jamaica! 

Jamaica is a beautiful Caribbean island that has lush green mountains and gorgeous golden sand beaches. The people are welcoming and the Caribbean blue water is perfect for swimming.

There are lots of great hotels that could be booked with points and it’s easy to get there with points and miles. Let’s look at how you can plan a long weekend in Jamaica without spending a lot of money. At the end of this post, I will outline a few ways to earn the points you’ll need to make this trip an easy reality.

How to Book Flights to Jamaica with Points and Miles

Jamaica is just a few hours flight from most of the U.S., making it a perfect option for a quick getaway. All major U.S. carriers fly to Jamaica, including Delta, American Airlines, United and Southwest.

We’ll cover economy class options here, because “first” class cabins on the aircraft serving the Caribbean are just domestic first class seats and are hardly worth the premium for these short flights.

Southwest Airlines

Southwest price in points will depend on the cash price, so be on the lookout for a good sale. And if you have Southwest Companion Pass you can get two people to Jamaica for the price of one!

Southwest has nonstop flights to Jamaica from the following airports:

  • Baltimore
  • Chicago Midway
  • Fort Lauderdale
  • Houston Hobby
  • Orlando
  • St. Louis

American Airlines

Booking an American Airlines flight is another great option, especially if you live near an AA hub or your home airport has good AA connections. You’ll need 12,500 AA miles for economy off peak, 15,000 miles peak or 25,000 miles for business class one way.

American has recently introduced “web specials” or reduced mileage awards so you might find rates that are even lower than the published award chart. The easiest way to find them is to click on calendar view. Web specials come with restrictions and might not have the best flight times, but if you want to save miles and have a flexible schedule, these could be a great bargain.

You can also book American Airlines flights with British Airways Avios. This will only make sense if you are booking a nonstop flight because BA will charge you separately for each segment.

This might sound counterintuitive, because how do you book a flight from the U.S. to Jamaica operated by a U.S.-based airline with a foreign airline’s miles? But this is where knowing a little bit about airline alliances and partner award bookings might come in handy.

As you can see, you’ll need just 11,000 BA Avios to book a nonstop flight to Jamaica. If you don’t have any AA miles, but have some Chase Ultimate Rewards points, you can still book AA flights by transferring Ultimate Rewards points to BA.

American Airlines has nonstop flights from the following airports:

  • Charlotte
  • Dallas/Fort Worth
  • Miami
  • New York (JFK)
  • Philadelphia
  • Boston (seasonal)
  • Chicago (ORD) (seasonal)

United Airlines

United had recently eliminated its award chart but you should expect to use at least 17,500 miles for one way in economy.

If you have one of the co-branded Chase cards, such as United℠ Explorer Card, United℠ Business Card or United Explorer Business Card, make sure you are logged into your United account when you search for award tickets. United shows more space on its own domestic flights to United credit card holders.

When you search for award space, you’ll see a one week calendar. To see a 30-day calendar, click on View 30 day calendar.

United has nonstop flights to Jamaica from the following airports:

  • Chicago (ORD)
  • Houston (IAH)
  • Newark (EWR)
  • Washington (IAD) (seasonal)

The information for the Southwest Rapid Rewards Premier Credit Card has been collected independently by 10XTravel.com. The card details on this page have not been reviewed or provided by the card issuer.


Delta, like United, doesn’t have an award chart anymore but you can still find some steals especially when Delta has their award sales. Which airport has sale prices varies, but keep an eye out for these, as you can save a ton of miles by snagging an award on sale.

Delta has nonstop flights from the following cities:

  • Atlanta
  • New York (JFK)
  • Boston (seasonal)
  • Detroit (seasonal)
  • Minneapolis/St. Paul (seasonal)

Chase Travel Portal for Flights

Don’t forget to check the prices in the portal. If you see a good cash price, it might make sense to book with Ultimate Rewards instead of transferring them to a partner airline, such as United, Southwest or British Airways.

You can book some of the low cost carriers, such as JetBlue and Spirit, through the portal. Flights booked through the portal earn miles, so that’s another reason to book cheap fares with Ultimate Rewards points rather than transferring them to partner airlines.

Where to Stay in Jamaica with Points and Miles

Jamaica has hundreds of hotels and resorts in all price ranges. To get the best experience and the best value, you can stay at an all inclusive resort for a true worry-free vacation.

Before you say that all inclusive resorts are boring, check out the list of included activities at each resort, as well as optional paid excursions. You can visit Dunn’s River Falls, go white water rafting and ziplining in the mountains, jump into the Blue Hole waterfall or visit Bob Marley Museum.

Use World of Hyatt Points to Book Your Stay in Jamaica

Hyatt Ziva Rose Hall and Hyatt Zilara Rose Hall

Hyatt Ziva Rose Hall is a family-friendly property and Hyatt Zilara Rose Hall is an adults-only resort. Both are all-inclusive resorts, so all food, drinks and many activities are included. Hyatt recently moved to standard, peak and off-peak pricing. The standard rate is 25,000 points, peak rate is 29,000 points and off-peak rate is 21,000 points.

If you’d like to add additional guests, you’ll have to pay half of the daily rate in points (10,500 off peak, 12,500 standard and 14,500 peak for each additional person).

Use IHG Club Points to Book Your Stay in Jamaica

Holiday Inn Resort Montego Bay All Inclusive

Photo courtesy of IHG

Another option that you can book with points is Holiday Inn Resort Montego Bay all inclusive resort. All meals, drinks and snacks are included and at 50,000 IHG points per night, it’s a good value. Two kids under 12 stay free, and you’ll pay $80 per night for each additional person 13 years old or older.

This newly refurbished hotel also offers RoseHall Club Adult Only section that includes a lounge, an adults-only pool and bar area and premium amenities and services.

If you have Chase IHG® Rewards Club Premier Credit Card, you can book three nights and get fourth night free.

Use Chase Travel Portal to Book Hotels

There are lots of beautiful all inclusive resorts in Jamaica. Some could be booked with hotel points, such as Hyatt or IHG points, and lots more could be booked with Ultimate Rewards points through the Chase travel portal.

If you have Chase Sapphire Reserve®, the points are worth 1.5 cents each. If you have the Chase Sapphire Preferred® Card or the Ink Business Preferred® Credit Card, then the points are worth 1.25 cents each.

To search for hotels, navigate to your Ultimate Rewards account and plug in your dates and destination.

There are lots of great independent all-inclusive resorts that aren’t part of any chain, or local chains such as Couples that provide great value. If the price might look high, remember that this includes everything – meals, drinks, entertainment, activities and water sports.

The major advantage of booking a hotel through the portal is the ability to pick the exact room type you want and see the price for more than two people in the room.

My husband and I stayed at Couples Negril, and it’s still one of our favorite places in the world. The price includes daily snorkeling and diving excursions, tennis lessons and clinics and all non-motorized water sports. The beach is phenomenal – the water is calm and warm and perfect for swimming.

RIU Palace Tropical Bay is located right next to Couples Negril. Unlike Couples Resorts, it’s a family resort and a stay there includes kids’ activities.

You’ll find many other properties in all price ranges on the travel portal. Before you book one of the Hyatt or IHG properties with hotel points, compare prices with the prices in the travel portal. You’ll probably come out ahead when you transfer Ultimate Rewards points to Hyatt because the cash price for these two properties hovers around $400 per night.

But if you don’t have any IHG points, or want to save them for another redemption, check the portal. Depending on the time of year and the occupancy, you’ll save a lot of points by booking through the portal.

Note that you likely won’t earn any hotel loyalty points and won’t receive elite benefits with a portal booking.

3 Things You Should Do in Jamaica

If you don’t want to spend your entire time in Jamaica relaxing by the pool or enjoying the beach, no worries, there are still lots of great activities to break up the day.

Diving and Snorkeling in Jamaica

Jamaica isn’t really known as a diving destination, but it should be. There are dives for all skill levels and some all-inclusive resorts like Couples and Sandals offer twice daily diving excursions.

You can even get PADI certified in Jamaica and practice your skills with friendly guides in more shallow waters. Snorkeling is another popular activity suitable for the whole family. Some resorts might even have snorkeling excursions included.

White Water or Bamboo Rafting

We’ve all heard of white water rafting, but what is bamboo rafting? How about drifting Martha Brae River on a 30-feet bamboo raft for two while sipping a cold drink? You can try your hand at guiding the raft or leave it to the professionals and just enjoy the beautiful tropical greenery all around you.

If you prefer a more active vacation, take a break from the beach and head over to the lush green mountains for some fresh water adventure. You can stick with something more relaxing and glide down a river in a raft or opt for a more adventure and go rushing through the rapids and around boulders down the wild and untamed part of the Great River.

Sunset Catamaran Cruise

Sailing the calm blue waters of the Caribbean, is another great way to enjoy the natural beauty of Jamaica. There are different kinds of sunset cruises, from the “booze cruise” with stops at the famous Rick’s Cafe and Margaritaville to the more subdued and romantic, there’s one for every taste.

If you enjoy being on the water, or want to party it up and enjoy some reggae music, a sunset cruise is great entertainment.

Been to Jamaica? Share your top tips with 10xTravel readers!

How to Earn Points for Your Weekend Trip to Jamaica

If you are going to book your flight or hotel (or both) through the portal, collecting a good stash of Ultimate Rewards points should be a priority. There are a few excellent Chase personal and business cards that come with generous welcome bonuses and great spending categories, such as the Chase Sapphire Reserve® and the Chase Ink Preferred.

You can transfer Chase Ultimate Rewards to partners such as Southwest, United, British Airways or even World of Hyatt and IHG Rewards Club. Chase also issues co-branded cards with each of these partners, such as the United℠ Explorer Card and the Southwest Rapid Rewards® Premier Credit Card.

The The World of Hyatt Credit Card even comes with an annual free night certificate that can be used at any Category 1-4 Hyatt property.

To be approved for any of the Chase cards you have to be under 5/24.

You can supplement your stash of Ultimate Rewards and airline miles by using shopping portals, especially if you are just a few thousand miles short.

American AAdvantage miles can be earned by opening a personal or business version of AAdvantage Aviator MasterCard or Citi AAdvantage Platinum Select World Elite Mastercard.

Delta is a transfer partner of American Express Membership Rewards. One of my favorite American Express cards is the Blue Business® Plus Credit Card from American Express. It has $0 annual fee (see rates and fees) and earns 2X points on all purchases on the first $50,000 spent in a calendar year and 1X thereafter.

Amex also issues co-branded Delta credit cards, such as the Delta SkyMiles® Gold American Express Card and the Delta SkyMiles® Platinum American Express Card, that often come with great welcome bonuses and benefits like a free checked bag.

Final Thoughts on a Jamaica Getaway

As you can see, it’s easy to plan a weekend getaway in Jamaica with points and miles – there are so many options. When it’s snowing outside, what could be better than a few days in the sun? In just a few hours, you can be on the beach enjoying a tropical drink. You’ll be charmed by Jamaican hospitality and awed by its natural beauty.

If you have a good stash of airline miles or credit card points, start planning your weekend getaway now!

Travel well,