How far in advance should I book a flight from Greenville to New Windsor?

When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 29 days in advance, which can save you up to 63% on flights from Greenville to New Windsor compared to booking the week you need them. Waiting 29 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $253. For sooner than that we have options available in the next 3 days from $359.

What is the cheapest month to fly from Greenville to New Windsor?

January is one of the best times of the year to fly to New Windsor from Greenville. Prices for January average $264 per person but you can even find prices for as low as $189. The most expensive prices can be found in the month of December. Opting for a January flight can save you 29% on your journey compared to booking in December

What is the cheapest time of day to fly from GSP to SWF?

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Greenville to New Windsor as you normally would.

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.

$239+ Flights from Greenville to New Windsor

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1. Tell us where you want to go

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Cheap flight deals from Greenville to Stewart

Round-trip from	$365 (Mytrip)
One-way from	$239 (Mytrip)
Popular in	December
Cheapest in	January
Average price	$239

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. 10% potential increase in price ($30 potential increase over avg. RT price).

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Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).

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Average for round-trip flights in July 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 July 2, 2025.

Thu 8/219:24 pmGSP - SWF

1 stop12h 48mMultiple Airlines

Sun 8/247:52 pmSWF - GSP

1 stop12h 56mMultiple Airlines

Deal found 6/30

$365

Mon 7/142:50 pmGSP - SWF

1 stop21h 06mBreeze Airways

Sun 7/277:52 pmSWF - GSP

1 stop12h 56mBreeze Airways

Deal found 6/30

$546

Best flights from Greenville to Stewart
Discover carefully curated flight deals from Greenville to Stewart that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 2, 2025.

Thu 8/219:24 pmGSP - SWF

1 stop12h 48mMultiple Airlines

Sun 8/247:52 pmSWF - GSP

1 stop12h 56mMultiple Airlines

Deal found 6/30

$365

Mon 7/142:50 pmGSP - SWF

1 stop21h 06mBreeze Airways

Sun 7/277:52 pmSWF - GSP

1 stop12h 56mBreeze Airways

Deal found 6/30

$546

Last-minute flights from Greenville to Stewart
Discover last-minute flight deals from Greenville to Stewart. Data last updated July 2, 2025 and is based on user searches.

Mon 7/72:50 pmGSP - SWF

1 stop21h 06mBreeze Airways

Thu 7/107:52 pmSWF - GSP

1 stop12h 56mBreeze Airways

Deal found 6/30

$774

Thu 7/104:33 pmGSP - SWF

2 stops26h 33mMultiple Airlines

Mon 7/147:56 pmSWF - GSP

2 stops18h 58mMultiple Airlines

Deal found 7/1

$540

Mon 7/142:50 pmGSP - SWF

1 stop21h 06mBreeze Airways

Sun 7/277:52 pmSWF - GSP

1 stop12h 56mBreeze Airways

Deal found 6/30

$546

Thu 8/219:24 pmGSP - SWF

1 stop12h 48mMultiple Airlines

Sun 8/247:52 pmSWF - GSP

1 stop12h 56mMultiple Airlines

Deal found 6/30

$365

One-way flights from Greenville to Stewart
Search for one-way flight options from Greenville to Stewart. Find affordable one-way fares based on user searches. Data last updated July 2, 2025.

Wed 7/309:42 pmGSP - SWF

3 stops20h 10mMultiple Airlines

Deal found 6/30

$239

Mon 8/42:50 pmGSP - SWF

1 stop21h 06mBreeze Airways

Deal found 7/1

$250

Cheapflights Fare Finder

Use the filters below to find and compare flights from Greenville to New Windsor that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

GreenvilleNew Windsor

GSP - SWF

GSPSWF

Greenville

Thu 8/21

9:24 pm-10:12 am

1 stop12h 48m

New Windsor Stewart

Sun 8/24

7:52 pm-8:48 am

1 stop12h 56m

$365

GreenvilleNew Windsor

GSP - SWF

GSPSWF

Greenville

Mon 7/14

2:50 pm-11:56 am

1 stop21h 06m

New Windsor Stewart

Sun 7/27

7:52 pm-8:48 am

1 stop12h 56m

$546

GreenvilleNew Windsor

GSP - SWF

GSPSWF

Greenville

Wed 7/30

9:42 pm-5:52 pm

3 stops20h 10m

$239

GreenvilleNew Windsor

GSP - SWF

GSPSWF

Greenville

Mon 8/4

2:50 pm-11:56 am

1 stop21h 06m

$250

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/30

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 August is currently the most expensive (average of $222). 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.

Reviews of airlines servicing Stewart

Get a feel of what it's like to fly with Breeze Airways from Greenville to New Windsor by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

Breeze Airways

8.1

Very good

182 reviews

Reviews

1 / 11

10.0

Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!

Breeze Airways

8.1

Very good

182 reviews

Breeze Airways

8.1

Very good

182 reviews

Reviews

1 / 11

10.0

Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!

Related info for your journey

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 August is currently the most expensive (average of $222). 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.

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Complete your trip

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$239+ 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 7/30. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Greenville to Stewart with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheap flight deals from Greenville to Stewart

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Find flight deals from Greenville to Stewart

Cheapest flights from Greenville to StewartExplore 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 July 2, 2025.

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 July 2, 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from Greenville to New Windsor that are best for you.

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.

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?

Reviews of airlines servicing Stewart

Get a feel of what it's like to fly with Breeze Airways from Greenville to New Windsor by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

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?

How can I find direct flights from Greenville to Stewart?

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

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

Traveling to a place near Greenville?

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Alternative routes for Greenville to Stewart

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Travel Smart

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 July 2, 2025.