Weekend Getaway: Jamaica

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Jamaica is a stunning Caribbean island with lush green mountains, golden sand beaches and warm turquoise waters perfect for swimming. The people are welcoming, the culture is vibrant and there are many excellent hotels that can be booked with points.

Best of all, 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 much cash and discover ways to earn the points you’ll need to make this trip a reality.

How to Book Flights to Jamaica with Points and Miles

Jamaica is just a few hours’ flight from much of the United States, making it perfect for a quick getaway. Many major U.S. carriers fly to Jamaica, including Delta Air Lines, American Airlines, United Airlines, Southwest Airlines and JetBlue.

We’ll focus on economy-class options since it’s typically not worth paying a premium for these short flights.

Southwest Airlines

Southwest prices award flights based on the cash fare, so it’s worth watching for sales. If you have a Southwest Companion Pass, you can get two people to Jamaica for the price of one.

Southwest has nonstop flights to Jamaica from:

• Baltimore (BWI)
• Chicago-Midway (MDW)
• Fort Lauderdale (FLL)
• Houston-Hobby (HOU)
• Nashville (BNA; begins March 7, 2026)
• Orlando (MCO)
• Kansas City (MCI; seasonal)
• St. Louis (STL; seasonal)

Because Southwest doesn’t have fixed award pricing, the amount you’ll pay will fluctuate depending on the cash fare for your flight, but as a general rule, you can expect to get around 1.3 cents per point in value.

American Airlines

American Airlines offers plenty of routing options to Jamaica, especially if you live near an American Airlines hub or have good connections.

Keep an eye out for web specials, which can offer even lower rates than you’ll typically see. You can use the airline’s low-fare calendar to find these special rates. While web specials often come with restrictions and less desirable flight times, if you want to save miles and have a flexible schedule, they’re worth considering. For our sample searches, we found award tickets in economy class from 8,000 American Airlines miles each way.

You can also book American Airlines flights with British Airways Avios. This typically only makes sense if you’re booking a nonstop flight because BA charges you separately for each segment based on the distance flown. Below are the Avios prices for American Airlines and Alaska Airlines flights:

If you don’t have American Airlines miles but have Chase Ultimate Rewards points, you can transfer them to BA to book American Airlines flights.

American Airlines offers nonstop flights to Montego Bay (MBJ) from:

• Charlotte (CLT)
• Chicago-O’Hare (ORD)
• Dallas/Fort Worth (DFW)
• Miami (MIA)
• New York-JFK (JFK)
• Philadelphia (PHL)
• Boston (BOS; seasonal)

There’s also a nonstop flight to Kingston (KIN) from Miami (MIA).

United Airlines

United Airlines uses dynamic pricing for award flights, so expect variability in award costs. During our searches, we saw economy class redemptions from 20,000 miles one-way.

If you have one of the co-branded Chase cards, such as a United℠ Explorer Card or United Quest℠ Card, make sure you’re logged into your United account when searching for award tickets, as United displays more space on its own flights to its credit card holders.

When searching for award space, you’ll see a one-week calendar, but you can click on “View 30-day calendar” to see more options.

United has nonstop flights to Jamaica from:

• Chicago-O’Hare (ORD)
• Denver (DEN)
• Houston-Intercontinental (IAH)
• Newark (EWR)
• Washington-Dulles (IAD)

Delta Air Lines

Delta doesn’t have a fixed award chart, but you can find deals that save you significant miles, especially during award sales. Which routes are discounted varies, so it pays to keep an eye out. We saw economy class redemptions starting at 17,000 miles each way during our searches.

Delta has nonstop flights to Montego Bay (MBJ) from:

• Atlanta (ATL)
• New York-JFK (JFK)
• Boston (BOS; seasonal)
• Detroit (DTW; seasonal)
• Minneapolis-St. Paul (MSP; seasonal)

Delta also offers flights to Kingston (KIN) from Atlanta (ATL) and New York-JFK (JFK; seasonal).

Chase Travel℠

Don’t forget to check flight prices in the Chase Travel℠ portal. If you see a good cash price, it might make sense to book with Chase Ultimate Rewards® instead of transferring them to a partner airline.

You can also book flights with low-cost carriers, such as JetBlue and Spirit Airlines, through the portal. Flights booked this way earn miles, which is another reason to book cheaper 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 across all price ranges, including some excellent all-inclusive resorts that offer plenty of activities for a hassle-free vacation.

Use World of Hyatt Points

Hyatt Ziva Rose Hall and Hyatt Zilara Rose Hall

Hyatt Ziva Rose Hall is family-friendly, while Hyatt Zilara Rose Hall is adults-only. Both are all-inclusive resorts where food, drinks and many activities are included.

Both properties are part of Hyatt’s all-inclusive award Category E, which costs 35,000 to 75,000 points per night for standard room redemptions.

These resorts offer excellent facilities and amenities, including multiple pools, beautiful beaches, plentiful restaurants and full shared access across both properties.

Use Marriott Bonvoy Points

Royalton Blue Waters, An Autograph Collection All-Inclusive Resort

Marriott has added several all-inclusive properties in Jamaica to its Autograph Collection brand. Royalton Blue Waters in Montego Bay offers family-friendly accommodation with beach access and multiple restaurants and pools.

This property typically starts at 48,000 Marriott Bonvoy points per night, making it a good option for redeeming a free night certificate issued by one of the Marriott credit cards.

Use Hilton Honors Points

S Hotel Montego Bay, an SLH Hotel

The S Hotel Montego Bay blends Jamaican style with sleek, urban design. Located near Doctor’s Cave Beach, this boutique property offers rooftop pool decks, art-filled interiors and a vibrant atmosphere.

The S Hotel Montego Bay can be booked from 105,000 Hilton Honors points per night.

For travelers visiting Kingston, consider ROK Hotel Kingston, Tapestry Collection by Hilton, which can be booked from 54,000 Hilton Honors points per night.

Use the Chase Travel℠ to Book Hotels

Many beautiful all-inclusive resorts in Jamaica can be booked with Ultimate Rewards points through the Chase Travel℠ portal.

With the Chase Sapphire Reserve® and the Chase Sapphire Preferred® Card, your points can be worth more when redeemed for travel with Chase’s Points Boost feature.

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

In addition to your favorite chain hotels, you’ll also be able to book independent all-inclusive resorts. If the price seems high, remember that it includes everything—meals, drinks, entertainment, activities and water sports.

3 Things You Should Do in Jamaica

If you don’t want to spend your entire time relaxing by the pool or enjoying the beach, Jamaica offers plenty of memorable activities.

Diving and Snorkeling

Jamaica offers diving options for all skill levels. Some all-inclusive resorts, such as Couples and Sandals, offer daily diving excursions.

You can get PADI certified in Jamaica and practice your skills with experienced guides in shallow waters. Snorkeling is also popular and suitable for the whole family, with some resorts offering snorkeling excursions.

White Water or Bamboo Rafting

Experience bamboo rafting on the Martha Brae River on a 30-foot bamboo raft for two, all while sipping a cold drink. A licensed raft captain guides the raft, though guests may get a chance to try guiding it themselves.

For a more active experience, head to the mountains for freshwater excitement. Choose a relaxing glide down the river or opt for adventure and ride through rapids and around boulders on the wild Great River.

Sunset Catamaran Cruise

Sailing the calm blue waters of the Caribbean is a wonderful way to enjoy Jamaica’s natural beauty. Options range from lively booze cruises with stops at famous spots, such as Rick’s Cafe and Margaritaville, to more romantic boat trips. If you want to dance to reggae music on the water, a sunset cruise offers great entertainment.

How to Earn Points for Your Weekend Trip to Jamaica

If you want to book your flight, hotel or both through the Chase Travel℠, building a strong stash of Ultimate Rewards points should be a priority. Chase offers excellent cards with great spending categories that make it easy to rack up points.

You can transfer Chase Ultimate Rewards to partners such as Southwest, United, BA, World of Hyatt, IHG One Rewards and Marriott Bonvoy; however, the last two options typically won’t give you the best value for your points. Additionally, Chase also offers co-branded cards with these partners.

To be approved for Chase cards, you must be under the 5/24 rule, meaning you haven’t opened five or more cards in the past 24 months across all banks.

American Airlines AAdvantage miles can be earned through co-branded cards such as the Citi® / AAdvantage® Platinum Select® World Elite Mastercard®, while Delta is a transfer partner of American Express Membership Rewards®. American Express also offers co-branded Delta credit cards that provide valuable benefits, such as free checked bags.

Final Thoughts on a Jamaican Getaway

It’s easy to plan a weekend getaway to Jamaica with points and miles, as there are so many options to choose from. When it’s cold outside, what could be better than a few days in the sun? In just a few hours, you could be relaxing on the beach with a tropical drink in hand, surrounded by the charm of Jamaican hospitality and the island’s stunning natural beauty.

If you have airline miles or credit card points, start planning your weekend getaway to Jamaica now.