HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Santiago de los Caballeros

$162+ Cheap flights from New Windsor (SWF) to Santiago de los Caballeros (STI)

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 4/9. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — STI
Mar 23 — Mar 301
Mon 3/23
Mon 3/30
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Stewart to Santiago de los Caballeros 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 Santiago de los Caballeros

Cheapest flights from Stewart to Santiago de los Caballeros
Explore the most affordable flight options available from Stewart to Santiago de los Caballeros. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 21, 2026.

This Kiwi.com deal was found by Cheapflights users on 2/20. 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.
Thu 3/510:09 am
SWF
-
STI
1 stop28h 26m
Multiple Airlines
Sat 3/74:40 pm
STI
-
SWF
1 stop16h 39m
Multiple Airlines
Deal found 2/20$373
This Kiwi.com deal was found by Cheapflights users on 2/18. 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.
Sun 4/510:29 am
SWF
-
STI
1 stop15h 20m
Multiple Airlines
Wed 4/82:46 am
STI
-
SWF
1 stop8h 09m
Multiple Airlines
Deal found 2/18$379
This Kiwi.com deal was found by Cheapflights users on 2/18. 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.
Thu 2/2611:52 am
SWF
-
STI
1 stop26h 43m
Multiple Airlines
Sat 3/142:46 am
STI
-
SWF
1 stop8h 53m
Multiple Airlines
Deal found 2/18$512
This Kiwi.com deal was found by Cheapflights users on 2/18. 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.
Thu 4/210:29 am
SWF
-
STI
1 stop27h 54m
Multiple Airlines
Sat 4/112:46 am
STI
-
SWF
1 stop8h 09m
Multiple Airlines
Deal found 2/18$564
This Kiwi.com deal was found by Cheapflights users on 2/19. 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.
Sat 4/411:45 am
SWF
-
STI
2 stops14h 04m
Multiple Airlines
Sat 4/112:46 am
STI
-
SWF
1 stop8h 09m
Multiple Airlines
Deal found 2/19$565
This Kiwi.com deal was found by Cheapflights users on 2/19. 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.
Thu 4/210:29 am
SWF
-
STI
1 stop27h 54m
Multiple Airlines
Sat 4/113:28 pm
STI
-
SWF
1 stop19h 27m
Multiple Airlines
Deal found 2/19$567
This Kiwi.com deal was found by Cheapflights users on 2/17. 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 4/310:00 am
SWF
-
STI
2 stops15h 49m
Multiple Airlines
Sat 4/112:46 am
STI
-
SWF
1 stop8h 09m
Multiple Airlines
Deal found 2/17$673
This Kiwi.com deal was found by Cheapflights users on 2/19. 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.
Thu 6/1110:28 am
SWF
-
STI
1 stop27h 54m
Multiple Airlines
Wed 6/173:27 pm
STI
-
SWF
1 stop18h 11m
Multiple Airlines
Deal found 2/19$750

Find flight deals from Stewart to Santiago de los Caballeros

Discover tips and strategies to find the most affordable flight options for your journey from Stewart (SWF) to Santiago de los Caballeros (STI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated February 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$379
(Kiwi.com)

One-way from

$162
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$447
Provider with most accurate pricing for New Windsor Stewart-Santiago de los Caballeros flight deals.
Search Deals
Provider most trusted by Cheapflights users for New Windsor Stewart-Santiago de los Caballeros flights.
Search Deals
From New Windsor Stewart to Santiago de los Caballeros
Search Deals
One-way flight from New Windsor Stewart to Santiago de los Caballeros
Search Deals
Highest demand for flights based on searches. 2% potential increase in price ($10 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Stewart to Santiago de los Caballeros 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 February 21, 2026.
Use the filters below to find and compare flights from New Windsor to Santiago de los Caballeros that are best for you.

Fly from

Stewart

Fly to

Santiago de los Caballeros

Route

Depart

Return

Price

New WindsorSantiago de los Caballeros

SWF - STI

SWFSTI

New Windsor Stewart

Thu 3/5

10:09 am-3:35 pm

1 stop28h 26m

Santiago de los Caballeros

Sat 3/7

4:40 pm-8:19 am

1 stop16h 39m

$373

New WindsorSantiago de los Caballeros

SWF - STI

SWFSTI

New Windsor Stewart

Thu 4/2

10:29 am-2:23 pm

1 stop27h 54m

Santiago de los Caballeros

Sat 4/11

2:46 am-10:55 am

1 stop8h 09m

$564

New WindsorSantiago de los Caballeros

SWF - STI

SWFSTI

New Windsor Stewart

Sat 4/4

11:45 am-1:49 am

2 stops14h 04m

Santiago de los Caballeros

Sat 4/11

2:46 am-10:55 am

1 stop8h 09m

$565

New WindsorSantiago de los Caballeros

SWF - STI

SWFSTI

New Windsor Stewart

Thu 4/2

10:29 am-2:23 pm

1 stop27h 54m

Santiago de los Caballeros

Sat 4/11

3:28 pm-10:55 am

1 stop19h 27m

$567

New WindsorSantiago de los Caballeros

SWF - STI

SWFSTI

New Windsor Stewart

Fri 4/3

10:00 am-1:49 am

2 stops15h 49m

Santiago de los Caballeros

Sat 4/11

2:46 am-10:55 am

1 stop8h 09m

$673

New WindsorSantiago de los Caballeros

SWF - STI

SWFSTI

New Windsor Stewart

Thu 6/11

10:28 am-2:22 pm

1 stop27h 54m

Santiago de los Caballeros

Wed 6/17

3:27 pm-9:38 am

1 stop18h 11m

$750

New WindsorSantiago de los Caballeros

SWF - STI

SWFSTI

New Windsor Stewart

Sun 6/14

10:28 am-2:22 pm

1 stop27h 54m

Santiago de los Caballeros

Wed 6/24

2:52 pm-9:38 am

1 stop18h 46m

$775

New WindsorSantiago de los Caballeros

SWF - STI

SWFSTI

New Windsor Stewart

Thu 4/9

11:45 am-1:49 am

1 stop14h 04m

$162

New WindsorSantiago de los Caballeros

SWF - STI

SWFSTI

New Windsor Stewart

Sun 4/5

10:29 am-2:23 pm

1 stop27h 54m

$170

New WindsorSantiago de los Caballeros

SWF - STI

SWFSTI

New Windsor Stewart

Sun 3/15

12:29 pm-2:35 pm

1 stop26h 06m

$171

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/18

Showing 1-10 of 14 results
1
2
  • Most accurate provider: When it comes to deals on New Windsor-Santiago de los Caballeros flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on New Windsor-Santiago de los Caballeros flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from New Windsor-Santiago de los Caballeros flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on New Windsor-Santiago de los Caballeros flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for New Windsor-Santiago de los Caballeros flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Stewart to Santiago de los Caballeros

Have a flexible travel schedule? Discover the best time to fly to Santiago de los Caballeros 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 Santiago de los Caballeros

What is the cheapest month to book a flight from New Windsor to Santiago de los Caballeros?

Currently, July is the cheapest month in which you can book a flight from New Windsor to Santiago de los Caballeros (average of $191). Flying from New Windsor to Santiago de los Caballeros in November is currently the most expensive (average of $248). 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 Santiago de los Caballeros. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • Can I find deals for flights from Stewart to Santiago de los Caballeros that include hotel bookings?

    Yes. In addition to deals on Stewart to Santiago de los Caballeros flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Stewart to Santiago de los Caballeros?

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

  • Can I find deals for business class flights from Stewart to Santiago de los Caballeros?

    Yes. Cheapflights offers flight deals from Stewart to Santiago de los Caballeros 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 Santiago de los Caballeros?

    Currently, July is the cheapest month in which you can book a flight from New Windsor to Santiago de los Caballeros (average of $191). Flying from New Windsor to Santiago de los Caballeros in November is currently the most expensive (average of $248). 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 Santiago de los Caballeros

See prices for flight routes from nearby airports that may be better suited for you.
Newark to Santiago de los Caballeros flights
John F Kennedy Intl to Punta Cana flights
John F Kennedy Intl to Santiago de los Caballeros flights
John F Kennedy Intl to Santo Domingo flights
Newark to Punta Cana flights
Newark to Santo Domingo flights
LaGuardia to Punta Cana flights
LaGuardia to Santo Domingo flights
LaGuardia to Santiago de los Caballeros flights
John F Kennedy Intl to Puerto Plata flights
Newark to Puerto Plata flights
LaGuardia to Puerto Plata flights
Buffalo to Punta Cana flights
Syracuse to Punta Cana flights
Rochester to Punta Cana flights
Albany to Punta Cana flights
White Plains to Punta Cana flights
John F Kennedy Intl to La Romana flights
Buffalo to Puerto Plata flights
Rochester to Santo Domingo flights
White Plains to Santo Domingo flights
Albany to Santo Domingo flights
Stewart to Santo Domingo flights
Stewart to Punta Cana flights
Newark to Nagua flights
Buffalo to Santo Domingo flights
Syracuse to Santo Domingo flights
Islip to Punta Cana flights
LaGuardia to Nagua flights
Islip to Santo Domingo flights
Syracuse to Santiago de los Caballeros flights
Ithaca to Punta Cana flights
Albany to Santiago de los Caballeros flights
Rochester to Puerto Plata flights
Buffalo to Santiago de los Caballeros flights
Albany to Puerto Plata flights
Islip to Santiago de los Caballeros flights
Syracuse to Puerto Plata flights
Rochester to La Romana flights
Stewart to Puerto Plata flights
Islip to Puerto Plata flights
Niagara Falls to Punta Cana flights
Buffalo to La Romana 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.