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Stewart

$156+ Cheap flights from Greenville to New Windsor (GSP - SWF)

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 11/10. Fares are subject to change and may not be available on all flights or dates of travel.
GSP — SWF
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
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Cheap flight deals from Greenville to Stewart

Discover tips and strategies to find the most affordable flight options for your journey from Greenville (GSP) to Stewart (SWF). 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 September 17, 2025.

Round-trip from

$338
(Kiwi.com)

One-way from

$156
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$289
From Greenville to New Windsor Stewart
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One-way flight from Greenville to New Windsor Stewart
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Highest demand for flights based on searches. 11% potential increase in price ($34 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Greenville to Stewart

Cheapest flights from Greenville to Stewart
Explore the most affordable flight options available from Greenville to Stewart. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 17, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
Mon 10/69:10 pmGSP - SWF
1 stop13h 16mAllegiant Air
Sun 10/127:11 pmSWF - GSP
1 stop25h 09mAllegiant Air
Deal found 9/16$338
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 12/1910:41 amGSP - SWF
1 stop7h 25mAllegiant Air
Mon 12/227:10 pmSWF - GSP
1 stop19h 26mAllegiant Air
Deal found 9/16$366
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 12/184:05 pmGSP - SWF
1 stop27h 16mAllegiant Air
Mon 12/227:10 pmSWF - GSP
1 stop19h 26mAllegiant Air
Deal found 9/16$372
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 10/28:03 pmGSP - SWF
2 stops15h 41mMultiple Airlines
Sun 10/57:11 pmSWF - GSP
1 stop25h 09mMultiple Airlines
Deal found 9/16$431
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 11/205:17 pmGSP - SWF
2 stops17h 05mMultiple Airlines
Sun 11/308:41 pmSWF - GSP
1 stop24h 39mMultiple Airlines
Deal found 9/16$453
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 12/185:17 pmGSP - SWF
2 stops24h 49mMultiple Airlines
Mon 12/227:10 pmSWF - GSP
1 stop19h 26mMultiple Airlines
Deal found 9/16$457
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
Tue 11/253:14 pmGSP - SWF
1 stop27h 21mAllegiant Air
Sun 11/308:41 pmSWF - GSP
1 stop24h 39mAllegiant Air
Deal found 9/16$499
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 9/218:03 pmGSP - SWF
2 stops15h 41mMultiple Airlines
Sun 9/287:12 pmSWF - GSP
1 stop19h 05mMultiple Airlines
Deal found 9/14$526
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 12/255:17 pmGSP - SWF
2 stops17h 50mMultiple Airlines
Mon 12/2911:37 amSWF - GSP
1 stop6h 58mMultiple Airlines
Deal found 9/16$585
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
Tue 11/254:18 pmGSP - SWF
2 stops19h 09mMultiple Airlines
Sun 11/308:41 pmSWF - GSP
1 stop24h 39mMultiple Airlines
Deal found 9/16$594

Cheapflights Fare Finder

 
Customize your flight search to find flights from Greenville to Stewart 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 September 17, 2025.
Use the filters below to find and compare flights from Greenville to New Windsor that are best for you.

Fly from

Greenville

Fly to

Stewart

Route

Depart

Return

Price

GreenvilleNew Windsor

GSP - SWF

GSPSWF

Greenville

Mon 10/6

9:10 pm-10:26 am

1 stop13h 16m

New Windsor Stewart

Sun 10/12

7:11 pm-8:20 pm

1 stop25h 09m

$338

GreenvilleNew Windsor

GSP - SWF

GSPSWF

Greenville

Fri 12/19

10:41 am-6:06 pm

1 stop7h 25m

New Windsor Stewart

Mon 12/22

7:10 pm-2:36 pm

1 stop19h 26m

$366

GreenvilleNew Windsor

GSP - SWF

GSPSWF

Greenville

Thu 12/18

4:05 pm-7:21 pm

1 stop27h 16m

New Windsor Stewart

Mon 12/22

7:10 pm-2:36 pm

1 stop19h 26m

$372

GreenvilleNew Windsor

GSP - SWF

GSPSWF

Greenville

Thu 10/2

8:03 pm-11:44 am

2 stops15h 41m

New Windsor Stewart

Sun 10/5

7:11 pm-8:20 pm

1 stop25h 09m

$442

GreenvilleNew Windsor

GSP - SWF

GSPSWF

Greenville

Thu 11/20

5:17 pm-10:22 am

2 stops17h 05m

New Windsor Stewart

Sun 11/30

8:41 pm-9:20 pm

1 stop24h 39m

$453

GreenvilleNew Windsor

GSP - SWF

GSPSWF

Greenville

Thu 12/18

5:17 pm-6:06 pm

2 stops24h 49m

New Windsor Stewart

Mon 12/22

7:10 pm-2:36 pm

1 stop19h 26m

$457

GreenvilleNew Windsor

GSP - SWF

GSPSWF

Greenville

Tue 11/25

3:14 pm-6:35 pm

1 stop27h 21m

New Windsor Stewart

Sun 11/30

8:41 pm-9:20 pm

1 stop24h 39m

$499

GreenvilleNew Windsor

GSP - SWF

GSPSWF

Greenville

Thu 12/25

5:17 pm-11:07 am

2 stops17h 50m

New Windsor Stewart

Mon 12/29

11:37 am-6:35 pm

1 stop6h 58m

$585

GreenvilleNew Windsor

GSP - SWF

GSPSWF

Greenville

Tue 11/25

4:18 pm-11:27 am

2 stops19h 09m

New Windsor Stewart

Sun 11/30

8:41 pm-9:20 pm

1 stop24h 39m

$594

GreenvilleNew Windsor

GSP - SWF

GSPSWF

Greenville

Thu 12/25

5:17 pm-11:07 am

2 stops17h 50m

New Windsor Stewart

Tue 12/30

4:50 pm-2:05 pm

1 stop21h 15m

$704

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

Showing 1-10 of 17 results
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Best time to book a flight from Greenville to Stewart

Have a flexible travel schedule? Discover the best time to fly to Stewart from Greenville 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 Greenville to New Windsor

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

Currently, October is the cheapest month in which you can book a flight from Greenville to New Windsor (average of $109). Flying from Greenville to New Windsor in December is currently the most expensive (average of $202). 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 Greenville to Stewart. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Greenville to New Windsor?

    A quick flight from Greenville to New Windsor can take about 13h 16m. Allegiant Air provides one of the quickest options available for as low as $338. The distance from Greenville to New Windsor is about 633 mi.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Greenville to Stewart 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 Greenville to New Windsor?

    Currently, October is the cheapest month in which you can book a flight from Greenville to New Windsor (average of $109). Flying from Greenville to New Windsor in December is currently the most expensive (average of $202). 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

Traveling to a place near New Windsor?

Book flights to New Windsor if you plan to visit one of these locations
Kingston

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