HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Jamaica

$138+ Cheap flights from New Windsor (SWF) to Jamaica

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/15. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — MBJ
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Stewart to Jamaica with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Stewart to Jamaica

Keep the following information in mind while searching for Stewart to Jamaica flight deals. Data was last updated July 31, 2025.

Round-trip from

$355
(Kiwi.com)

One-way from

$138
(Mytrip)

Popular in

December

Cheapest in

September

Average price

$546
From New Windsor Stewart to Jamaica
Search Deals
One-way flight from New Windsor Stewart to Jamaica
Search Deals
High demand for flights, 0% potential price rise
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2025
Search Deals

Find flight deals from Stewart to Jamaica

Cheapest flights from Stewart to Jamaica
Explore the most affordable flight options available from Stewart to Jamaica. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 31, 2025.

This Kiwi.com deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/157:37 pmSWF - MBJ
1 stop16h 37mMultiple Airlines
Thu 8/2110:22 amMBJ - SWF
1 stop29h 24mMultiple Airlines
Deal found 7/30$355
This Mytrip deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/157:37 pmSWF - KIN
1 stop16h 50mMultiple Airlines
Fri 8/227:55 amKIN - SWF
1 stop7h 51mMultiple Airlines
Deal found 7/30$374

Cheapflights Fare Finder

 
Customize your flight search to find flights from Stewart to Jamaica that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 31, 2025.
Use the filters below to find and compare flights from New Windsor to Jamaica that are best for you.

Fly from

Stewart

Fly to

Jamaica

Route

Depart

Return

Price

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

Fri 8/15

7:37 pm-11:14 am

1 stop16h 37m

Montego Bay Sangster Intl

Thu 8/21

10:22 am-4:46 pm

1 stop29h 24m

$355

New WindsorKingston

SWF - KIN

SWFKIN

New Windsor Stewart

Fri 8/15

7:37 pm-11:27 am

1 stop16h 50m

Kingston Norman Manley

Fri 8/22

7:55 am-4:46 pm

1 stop7h 51m

$374

New WindsorMontego Bay

SWF - MBJ

SWFMBJ

New Windsor Stewart

Fri 8/15

7:37 pm-11:14 am

1 stop16h 37m

$138

New WindsorKingston

SWF - KIN

SWFKIN

New Windsor Stewart

Fri 8/15

7:37 pm-11:27 am

1 stop16h 50m

$142

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

Best time to book a flight from Stewart to Jamaica

Have a flexible travel schedule? Discover the best time to fly to Jamaica from Stewart with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from New Windsor to Jamaica

What is the cheapest month to book a flight from New Windsor to Jamaica?

Currently, January is the cheapest month in which you can book a flight from New Windsor to Jamaica (average of $403). Flying from New Windsor to Jamaica in July is currently the most expensive (average of $562). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Related info for your journey

Find useful and relevant information for your journey from Stewart to Jamaica. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from New Windsor to Jamaica?

    For a flight from New Windsor to Jamaica, you will be flying from Stewart. New Windsor Stewart (SWF) is just 4.3 mi from the center of the city.

  • Can I find deals for flights from Stewart to Jamaica that include hotel bookings?

    Yes. In addition to deals on Stewart to Jamaica flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Stewart to Jamaica?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Stewart to Jamaica.

  • Can I find deals for business class flights from Stewart to Jamaica?

    Yes. Cheapflights offers flight deals from Stewart to Jamaica by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from New Windsor to Jamaica?

    Currently, January is the cheapest month in which you can book a flight from New Windsor to Jamaica (average of $403). Flying from New Windsor to Jamaica in July is currently the most expensive (average of $562). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Stewart to Jamaica

See prices for flight routes from nearby airports that may be better suited for you.
John F Kennedy Intl to Luis Munoz Marin Intl flights
Newark to Luis Munoz Marin Intl flights
LaGuardia to Luis Munoz Marin Intl flights
John F Kennedy Intl to Montego Bay flights
John F Kennedy Intl to Santiago de los Caballeros flights
Newark to Santo Domingo flights
John F Kennedy Intl to Punta Cana flights
Newark to Santiago de los Caballeros flights
Newark to Oranjestad flights
John F Kennedy Intl to Oranjestad flights
John F Kennedy Intl to Santo Domingo flights
Newark to Punta Cana flights
Newark to Montego Bay flights
LaGuardia to Montego Bay flights
LaGuardia to Punta Cana flights
LaGuardia to Oranjestad flights
John F Kennedy Intl to Nassau flights
Newark to Nassau flights
John F Kennedy Intl to Providenciales flights
LaGuardia to Santo Domingo flights
John F Kennedy Intl to Port of Spain flights
John F Kennedy Intl to Kingston flights
John F Kennedy Intl to Bridgetown flights
Newark to Simpson Bay flights
John F Kennedy Intl to Simpson Bay flights
LaGuardia to Santiago de los Caballeros flights
Newark to Providenciales flights
John F Kennedy Intl to Willemstad flights
LaGuardia to Nassau flights
John F Kennedy Intl to Saint Thomas Island flights
Newark to Saint Thomas Island flights
John F Kennedy Intl to St. John's flights
John F Kennedy Intl to Aguadilla flights
John F Kennedy Intl to St. George's flights
LaGuardia to Providenciales flights
LaGuardia to Simpson Bay flights
Newark to Bridgetown flights
John F Kennedy Intl to Castries flights
John F Kennedy Intl to Puerto Plata flights
LaGuardia to Saint Thomas Island flights
White Plains to Luis Munoz Marin Intl flights
LaGuardia to Bridgetown flights
Newark to Willemstad flights
Newark to Kingston flights
Newark to George Town flights
LaGuardia to Kingston flights
John F Kennedy Intl to Ponce flights
John F Kennedy Intl to George Town flights
Newark to St. John's flights
LaGuardia to Willemstad flights

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.