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Stewart

$229+ 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 2/16. Fares are subject to change and may not be available on all flights or dates of travel.
GSP — SWF
Feb 20 — Feb 271
Fri 2/20
Fri 2/27
1 adult, Economy
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Cheap 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 January 21, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/20. 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.
Wed 6/173:48 pm
GSP
-
SWF
1 stop17h 50m
Allegiant Air
Sun 6/218:04 pm
SWF
-
GSP
1 stop18h 27m
Allegiant Air
Deal found 1/20$385
This Kiwi.com deal was found by Cheapflights users on 1/20. 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 1/226:45 pm
GSP
-
SWF
1 stop15h 34m
Multiple Airlines
Sun 1/2512:13 pm
SWF
-
GSP
1 stop27h 46m
Multiple Airlines
Deal found 1/20$517
This Kiwi.com deal was found by Cheapflights users on 1/20. 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 1/295:45 pm
GSP
-
SWF
1 stop16h 34m
Multiple Airlines
Sun 2/112:13 pm
SWF
-
GSP
1 stop27h 46m
Multiple Airlines
Deal found 1/20$526
This Kiwi.com deal was found by Cheapflights users on 1/20. 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 2/192:12 pm
GSP
-
SWF
2 stops21h 19m
Multiple Airlines
Thu 2/2611:52 am
SWF
-
GSP
1 stop30h 07m
Multiple Airlines
Deal found 1/20$588

Find 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 January 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$526
(Kiwi.com)

One-way from

$229
(Kiwi.com)

Popular in

December

Cheapest in

April

Average price

$249
Provider with most accurate pricing for Greenville-New Windsor Stewart flight deals.
Search Deals
Provider most trusted by Cheapflights users for Greenville-New Windsor Stewart flights.
Search Deals
From Greenville to New Windsor Stewart
Search Deals
One-way flight from Greenville to New Windsor Stewart
Search Deals
Highest demand for flights based on searches. 14% potential increase in price ($46 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

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 January 21, 2026.
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

Thu 1/29

5:45 pm-10:19 am

1 stop16h 34m

New Windsor Stewart

Sun 2/1

12:13 pm-3:59 pm

1 stop27h 46m

$526

GreenvilleNew Windsor

GSP - SWF

GSPSWF

Greenville

Thu 2/19

2:12 pm-11:31 am

2 stops21h 19m

New Windsor Stewart

Thu 2/26

11:52 am-5:59 pm

1 stop30h 07m

$588

GreenvilleNew Windsor

GSP - SWF

GSPSWF

Greenville

Mon 2/16

4:07 pm-11:51 am

1 stop19h 44m

$229

GreenvilleNew Windsor

GSP - SWF

GSPSWF

Greenville

Fri 4/17

8:18 pm-10:55 am

2 stops38h 37m

$232

GreenvilleNew Windsor

GSP - SWF

GSPSWF

Greenville

Fri 1/30

8:47 pm-11:33 am

2 stops38h 46m

$237

GreenvilleNew Windsor

GSP - SWF

GSPSWF

Greenville

Sun 2/15

3:37 pm-10:14 am

1 stop18h 37m

$240

GreenvilleNew Windsor

GSP - SWF

GSPSWF

Greenville

Fri 3/6

8:18 pm-8:19 am

2 stops36h 01m

$259

GreenvilleNew Windsor

GSP - SWF

GSPSWF

Greenville

Sun 2/22

12:53 pm-10:14 am

1 stop21h 21m

$295

GreenvilleNew Windsor

GSP - SWF

GSPSWF

Greenville

Sun 2/22

5:17 pm-11:31 am

3 stops18h 14m

$342

GreenvilleNew Windsor

GSP - SWF

GSPSWF

Greenville

Sun 2/22

2:12 pm-11:31 am

2 stops21h 19m

$355

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/21

Showing 1-10 of 12 results
1
2

Compare providers for flights from Greenville to Stewart

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 Greenville to Stewart in January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 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 Greenville-New Windsor flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Greenville-New Windsor flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Greenville-New Windsor flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Greenville-New Windsor flights, Cheapflights users trust Expedia the most. Expedia 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 Greenville-New Windsor 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 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, February is the cheapest month in which you can book a flight from Greenville to New Windsor (average of $32). Flying from Greenville to New Windsor in December is currently the most expensive (average of $78). 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.

  • 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, February is the cheapest month in which you can book a flight from Greenville to New Windsor (average of $32). Flying from Greenville to New Windsor in December is currently the most expensive (average of $78). 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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