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Santiago de los Caballeros

$150+ 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 12/15. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — STI
Dec 29 — Jan 51
Mon 12/29
Mon 1/5
1 adult, Economy
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Find 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 November 29, 2025.

This Mytrip deal was found by Cheapflights users on 11/26. 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 12/1212:27 pmSWF - STI
1 stop13h 15mMultiple Airlines
Sun 12/143:43 amSTI - SWF
1 stop8h 54mMultiple Airlines
Deal found 11/26$323
This Mytrip deal was found by Cheapflights users on 11/27. 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.
Mon 12/812:27 pmSWF - STI
1 stop13h 15mMultiple Airlines
Thu 12/113:43 amSTI - SWF
1 stop8h 54mMultiple Airlines
Deal found 11/27$329
This Mytrip deal was found by Cheapflights users on 11/27. 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.
Mon 12/1512:27 pmSWF - STI
1 stop13h 15mMultiple Airlines
Thu 12/183:43 amSTI - SWF
1 stop15h 23mMultiple Airlines
Deal found 11/27$332
This Mytrip deal was found by Cheapflights users on 11/28. 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.
Mon 12/812:27 pmSWF - STI
1 stop13h 15mMultiple Airlines
Thu 12/183:43 amSTI - SWF
1 stop15h 23mMultiple Airlines
Deal found 11/28$346
This Mytrip deal was found by Cheapflights users on 11/27. 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 12/1212:27 pmSWF - STI
1 stop13h 15mMultiple Airlines
Sun 12/213:43 amSTI - SWF
1 stop16h 52mMultiple Airlines
Deal found 11/27$366
This Kiwi.com deal was found by Cheapflights users on 11/29. 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 12/1212:27 pmSWF - STI
1 stop13h 15mMultiple Airlines
Thu 1/224:40 pmSTI - SWF
1 stop18h 39mMultiple Airlines
Deal found 11/29$374
This Mytrip deal was found by Cheapflights users on 11/27. 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 12/196:56 pmSWF - STI
1 stop6h 46mMultiple Airlines
Sun 12/283:43 amSTI - SWF
1 stop8h 04mMultiple Airlines
Deal found 11/27$608
This Mytrip deal was found by Cheapflights users on 11/28. 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 12/196:56 pmSWF - STI
1 stop6h 46mMultiple Airlines
Sun 12/213:43 amSTI - SWF
1 stop16h 52mMultiple Airlines
Deal found 11/28$617
This Kiwi.com deal was found by Cheapflights users on 11/27. 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 12/209:45 amSWF - STI
2 stops15h 57mMultiple Airlines
Sun 12/283:43 amSTI - SWF
1 stop8h 04mMultiple Airlines
Deal found 11/27$618

Cheap 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 November 29, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$323
(Mytrip)

One-way from

$150
(Mytrip)

Popular in

December

Cheapest in

March

Average price

$411
Provider with most accurate pricing for New Windsor Stewart-Santiago de los Caballeros flight deals.
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Provider most trusted by Cheapflights users for New Windsor Stewart-Santiago de los Caballeros flights.
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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. 4% potential increase in price ($20 potential increase over avg. RT price).
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 November 2025
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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 November 29, 2025.
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

Fri 12/12

12:27 pm-2:42 am

1 stop13h 15m

Santiago de los Caballeros

Sun 12/14

3:43 am-11:37 am

1 stop8h 54m

$323

New WindsorSantiago de los Caballeros

SWF - STI

SWFSTI

New Windsor Stewart

Mon 12/15

12:27 pm-2:42 am

1 stop13h 15m

Santiago de los Caballeros

Thu 12/18

3:43 am-6:06 pm

1 stop15h 23m

$332

New WindsorSantiago de los Caballeros

SWF - STI

SWFSTI

New Windsor Stewart

Fri 12/12

12:27 pm-2:42 am

1 stop13h 15m

Santiago de los Caballeros

Sun 12/21

3:43 am-7:35 pm

1 stop16h 52m

$366

New WindsorSantiago de los Caballeros

SWF - STI

SWFSTI

New Windsor Stewart

Fri 12/12

12:27 pm-2:42 am

1 stop13h 15m

Santiago de los Caballeros

Thu 1/22

4:40 pm-10:19 am

1 stop18h 39m

$374

New WindsorSantiago de los Caballeros

SWF - STI

SWFSTI

New Windsor Stewart

Fri 12/19

6:56 pm-2:42 am

1 stop6h 46m

Santiago de los Caballeros

Sun 12/28

3:43 am-10:47 am

1 stop8h 04m

$608

New WindsorSantiago de los Caballeros

SWF - STI

SWFSTI

New Windsor Stewart

Fri 12/19

6:56 pm-2:42 am

1 stop6h 46m

Santiago de los Caballeros

Sun 12/21

3:43 am-7:35 pm

1 stop16h 52m

$617

New WindsorSantiago de los Caballeros

SWF - STI

SWFSTI

New Windsor Stewart

Sat 12/20

9:45 am-2:42 am

2 stops15h 57m

Santiago de los Caballeros

Sun 12/28

3:43 am-10:47 am

1 stop8h 04m

$617

New WindsorSantiago de los Caballeros

SWF - STI

SWFSTI

New Windsor Stewart

Sun 2/15

11:42 am-3:35 pm

1 stop26h 53m

Santiago de los Caballeros

Sat 2/21

4:40 pm-11:02 am

1 stop19h 22m

$679

New WindsorSantiago de los Caballeros

SWF - STI

SWFSTI

New Windsor Stewart

Mon 12/15

12:27 pm-2:42 am

1 stop13h 15m

$150

New WindsorSantiago de los Caballeros

SWF - STI

SWFSTI

New Windsor Stewart

Fri 12/12

12:27 pm-2:42 am

1 stop13h 15m

$162

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/27

Showing 1-10 of 13 results
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Compare providers for flights from Stewart to Santiago de los Caballeros

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Stewart to Santiago de los Caballeros in November.
ProviderPrice AccuracyTrust Score*
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on New Windsor-Santiago de los Caballeros flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on New Windsor-Santiago de los Caballeros flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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, March is the cheapest month in which you can book a flight from New Windsor to Santiago de los Caballeros (average of $188). Flying from New Windsor to Santiago de los Caballeros in August is currently the most expensive (average of $256). 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, March is the cheapest month in which you can book a flight from New Windsor to Santiago de los Caballeros (average of $188). Flying from New Windsor to Santiago de los Caballeros in August is currently the most expensive (average of $256). 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

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Alternative routes for Stewart to Santiago de los Caballeros

See prices for flight routes from nearby airports that may be better suited for you.
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