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$410+ Cheap flights from New Windsor (SWF) to Italy

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 1/23. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — NAP
Nov 27 — Dec 41
Thu 11/27
Thu 12/4
1 adult, Economy
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Cheap flight deals from Stewart to Italy

Keep the following information in mind while searching for Stewart to Italy flight deals. Data was last updated October 28, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Popular in

June

Cheapest in

November

Average price

$529
Provider with most accurate pricing for New York (NYC)-Rome (ROM) flight deals.
Search Deals
Provider most trusted by Cheapflights users for New York (NYC)-Rome (ROM) flights.
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Highest demand for flights based on searches. 16% potential increase in price ($131 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($21 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Find flight deals from Stewart to Italy

One-way flights from Stewart to Italy
Search for one-way flight options from Stewart to Italy. Find affordable one-way fares based on user searches. Data last updated October 28, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/27. 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.
Fri 1/237:33 pmSWF - MXP
2 stops40h 12mMultiple Airlines
Deal found 10/27$410
This Kiwi.com deal was found by Cheapflights users on 10/27. 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.
Fri 1/237:33 pmSWF - BGY
2 stops56h 57mMultiple Airlines
Deal found 10/27$426
This Kiwi.com deal was found by Cheapflights users on 10/27. 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.
Mon 12/228:25 pmSWF - FCO
3 stops41h 05mMultiple Airlines
Deal found 10/27$712
This Kiwi.com deal was found by Cheapflights users on 10/27. 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.
Thu 12/1811:43 amSWF - MXP
2 stops23h 27mMultiple Airlines
Deal found 10/27$724
This Kiwi.com deal was found by Cheapflights users on 10/27. 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.
Thu 12/1811:43 amSWF - CIA
2 stops26h 17mMultiple Airlines
Deal found 10/27$796
This Kiwi.com deal was found by Cheapflights users on 10/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/196:56 pmSWF - FCO
3 stops45h 04mMultiple Airlines
Deal found 10/26$837
This Kiwi.com deal was found by Cheapflights users on 10/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/196:56 pmSWF - VCE
3 stops40h 19mMultiple Airlines
Deal found 10/26$837
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/196:56 pmSWF - CTA
3 stops44h 09mMultiple Airlines
Deal found 10/28$937
This Kiwi.com deal was found by Cheapflights users on 10/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/196:56 pmSWF - MXP
3 stops38h 09mMultiple Airlines
Deal found 10/26$1,011
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/196:56 pmSWF - FLR
3 stops39h 54mMultiple Airlines
Deal found 10/28$1,276
This Kiwi.com deal was found by Cheapflights users on 10/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/310:50 amSWF - FCO
3 stops52h 20mMultiple Airlines
Deal found 10/26$1,835

Cheapflights Fare Finder

 
Customize your flight search to find flights from Stewart to Italy 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 October 28, 2025.
Use the filters below to find and compare flights from New Windsor to Italy that are best for you.

Fly from

Stewart

Fly to

Italy

Route

Depart

Return

Price

New WindsorMilan

SWF - MXP

SWFMXP

New Windsor Stewart

Fri 1/23

7:33 pm-5:45 pm

2 stops40h 12m

$410

New WindsorBergamo

SWF - BGY

SWFBGY

New Windsor Stewart

Fri 1/23

7:33 pm-10:30 am

2 stops56h 57m

$426

New WindsorRome

SWF - FCO

SWFFCO

New Windsor Stewart

Mon 12/22

8:25 pm-7:30 pm

3 stops41h 05m

$712

New WindsorMilan

SWF - MXP

SWFMXP

New Windsor Stewart

Thu 12/18

11:43 am-5:10 pm

2 stops23h 27m

$724

New WindsorRome

SWF - CIA

SWFCIA

New Windsor Stewart

Thu 12/18

11:43 am-8:00 pm

2 stops26h 17m

$796

New WindsorRome

SWF - FCO

SWFFCO

New Windsor Stewart

Fri 12/19

6:56 pm-10:00 pm

3 stops45h 04m

$837

New WindsorVenice

SWF - VCE

SWFVCE

New Windsor Stewart

Fri 12/19

6:56 pm-5:15 pm

3 stops40h 19m

$837

New WindsorCatania

SWF - CTA

SWFCTA

New Windsor Stewart

Fri 12/19

6:56 pm-9:05 pm

3 stops44h 09m

$937

New WindsorMilan

SWF - MXP

SWFMXP

New Windsor Stewart

Fri 12/19

6:56 pm-3:05 pm

3 stops38h 09m

$1,011

New WindsorFlorence

SWF - FLR

SWFFLR

New Windsor Stewart

Fri 12/19

6:56 pm-4:50 pm

3 stops39h 54m

$1,276

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/27

Best time to book a flight from Stewart to Italy

Have a flexible travel schedule? Discover the best time to fly to Italy 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 Italy

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

Currently, January is the cheapest month in which you can book a flight from New Windsor to Italy (average of $78). Flying from New Windsor to Italy in June is currently the most expensive (average of $520). 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 Italy. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from New Windsor to Italy?

    Most people fly from New Windsor Stewart (SWF) if they book a flight from New Windsor to Italy. New Windsor Stewart is conveniently located just 4.3 mi from New Windsor’s city center.

  • What are the most popular routes from New Windsor to Italy?

    The most popular flight routes from New Windsor to Italy are New Windsor Stewart - Venice Marco Polo, New Windsor Stewart - Rome Fiumicino and New Windsor Stewart - Bergamo Orio Al Serio.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Stewart to Italy 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 Italy?

    Currently, January is the cheapest month in which you can book a flight from New Windsor to Italy (average of $78). Flying from New Windsor to Italy in June is currently the most expensive (average of $520). 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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